Pyrazole amide compounds and uses thereof

ABSTRACT

Disclosed is a pyrazole amide compound having fungicidal activity, with a structure shown by the general formula (I): 
     
       
         
         
             
             
         
       
     
     Each of the substituents of the compound being defined as in the description. The compound of the present invention has fungicidal activity, and excellent prevention and controlling effects on diseases, such as cucumber downy mildew, corn rust, wheat powdery mildew, rice blast, etc., and in particular, a better prevention and controlling effect on cucumber downy mildew and corn rust. Also disclosed is a process for preparing the compound, a fungicidal composition containing the compound of general formula (I) and the use thereof in preventing and controlling disease in crops.

FIELD OF THE INVENTION

The invention relates to fungicide. Specifically to a novel pyrazole amide compounds and uses thereof.

BACKGROUND OF THE INVENTION

Plant diseases cause a lot of damage to crops, especially to food and fiber, which can meet the human demand for basic agricultural products, such as fruits, vegetables, cotton, rice, corn, wheat, soybeans and so on. To kill or inhibit the growth of bacteria and to avoid or reduce the damage to crops is an effective way to improve agricultural production. Therefore, it is necessary to constantly develop more effective novel fungicides.

As we all know, pyrazole amide compounds such as tolfenpyrad and tebufenpyrad are used as insecticides and acaricides, as well as some pyrazole amide compounds reported in the following literatures: CN1927860A, CN1919838A, CN1091426A, U.S. Pat. No. 5,705,453, WO2002083647A, etc. However, the insecticidal and fungicidal activity of some compounds of this kind were disclosed in CN1919838A, CN1091426A, U.S. Pat. No. 5,705,453 and WO2002083647A, but the uses as agricultural fungicide of the pyrazole amide compounds having general formula of the present invention had not been reported in prior art.

SUMMARY OF THE INVENTION

The object of the present invention is to provide a novel pyrazole amide compounds, which can be used to prepare fungicides against harmful fungus and bacteria in agricultural or other fields.

Detailed descriptions of the invention are as follows:

The present invention provides a kind of pyrazole amide compounds having general formula (I):

Wherein:

R₁ is selected from H, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂cyanoalkyl, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂haloalkylcarbonyl, C₁-C₁₂alkoxycarbonyl, C₁-C₁₂haloalkoxycarbonyl, C₁-C₁₂alkylaminocarbonyl, C₁-C₁₂haloalkylaminocarbonyl, C₃-C₆cycloalkyl or R₈;

R₂ is selected from H, halogen, CN, C₁-C₁₂cyanoalkyl, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂cyanoalkoxy, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂haloalkoxyC₁-C₁₂alkyl, C₁-C₁₂alkylthioC₁-C₁₂alkyl, C₁-C₁₂haloalkylthioC₁-C₁₂alkyl, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₃-C₆cycloalkyl or R₈;

R₃ is selected from H or C₁-C₁₂alkyl; m is selected from 0 to 5;

R₄ is selected from halogen, CN, CONH₂, CSNH₂, NO₂, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂haloalkoxyC₁-C₁₂alkyl, C₁-C₁₂alkylthioC₁-C₁₂alkyl, C₁-C₁₂haloalkylthioC₁-C₁₂alkyl, C₁-C₁₂alkylamino, C₁-C₁₂haloalkylamino, C₂-C₁₂dialkylamino, piperidyl, pyrrolidyl, N-methyl piperazinyl, morpholinyl, C₂-C₁₂alkenyl, C₂-C₁₂haloalkenyl, C₂-C₁₂alkenoxy, C₂-C₁₂haloalkenoxy, C₂-C₁₂alkynyl, C₂-C₁₂haloalkynyl, C₂-C₁₂alkynoxy, C₂-C₁₂haloalkynoxy, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl or R₈; n is selected from 0 to 4;

R₅ is selected from H, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₃-C₆cycloalkyl, C₁-C₁₂cyanoalkyl, C₁-C₁₂alkylamino, C₁-C₁₂haloalkylamino, C₂-C₁₂dialkylamino, C₂-C₁₂alkenyl, C₂-C₁₂haloalkenyl, C₂-C₁₂alkynyl, C₂-C₁₂haloalkynyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂haloalkylcarbonyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkylcarbonylamino

or R₈;

R₆ is selected from H, CN, SCN, H(C═O), C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₁-C₁₂alkylcarbonyl, C₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂cyanoalkyl, C₁-C₁₂hydroxyalkyl, C₃-C₆cycloalkyl or R₈; p is selected from 0 to 5;

X₁ is selected from H, halogen, NO₂, CN, SCN, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylsulfinyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₁₂haloalkylthio, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂haloalkoxyC₁-C₁₂alkyl, C₁-C₁₂alkylthioC₁-C₁₂alkyl or C₁-C₁₂haloalkylthioC₁-C₁₂alkyl;

X₂, X₃, X₄ and X₅ may be the same or different, mutually independently selected from H, halogen, CN, NO₂, OH, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio or C₁-C₁₂alkylsulfonyl;

Q₁ and Q₂ may be the same or different, mutually independently selected from H, NH₂, OH, CN, SCN, C₁-C₁₂cyanoalkyl, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylsulfinyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₁₂alkylamino, C₂-C₁₂dialkylamino, piperidyl, pyrrolidyl, N-methyl piperazinyl, morpholinyl, H(C═O), C₁-C₁₂alkylaminocarbonyl, C₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkylaminothio, C₂-C₁₂dialkylaminothio, C₃-C₆cycloalkyl or R₈;

Y is selected from O, S or NR₇;

Z is selected from O or S;

R₇ is selected from H, CN, NH₂, OH, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₃-C₆cycloalkyl, C₁-C₁₂cyanoalkyl, C₁-C₁₂cyanoalkoxy, C₁-C₁₂alkylamino, C₁-C₁₂haloalkylamino, C₂-C₁₂dialkylamino, piperidyl, Pyrrolidyl, N-methylpiperazinyl, morpholinyl, 2,6-dimethylmorpholinyl, C₂-C₁₂alkenyl, C₂-C₁₂haloalkenyl, C₂-C₁₂alkenoxy, C₂-C₁₂haloalkenoxy, C₂-C₁₂alkynyl, C₂-C₁₂haloalkynyl, C₂-C₁₂alkynoxy, C₂-C₁₂haloalkynoxy, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂haloalkylcarbonyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkylcarbonylamino,

or R₈;

Or, when Y is selected from NR₇, NR₇ and R₅ form a unsubstituted or substituted five-membered or six-membered ring with 1-4 substitutents selected independently from C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy or C₃-C₆cycloalkyl;

R₈ is selected from phenyl, benzoyl, phenoxycarbonyl, phenylaminocarbonyl, phenylC₁-C₆alkyl, naphthyl, naphthylC₁-C₆alkyl, heteroaryl, heteroarylcarbonyl, heteroaryloxycarbonyl, heteroarylaminocarbonyl or heteroarylC₁-C₆alkyl, which can be unsubstituted or further substituted with 1-5 substitutents, the substitutent(s) mentioned was (were) selected independently from halogen, NO₂, CN, SH, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₃-C₁₂cycloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₂-C₁₂alkenyl, C₂-C₁₂haloalkenyl, C₂-C₁₂alkynyl, C₂-C₁₂haloalkynyl, C₃-C₁₂alkenoxy, C₃-C₁₂haloalkenoxy, C₃-C₁₂alkynoxy, C₃-C₁₂haloalkynoxy, C₁-C₁₂alkylsulfinyl, C₁-C₁₂haloalkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂haloalkylcarbonyl, C₁-C₁₂alkylcarbonyloxy, C₁-C₁₂alkylcarbonylamino, C₁-C₁₂alkylsulfonyloxy, C₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkoxyC₁-C₁₂alkoxy, C₁-C₁₂ alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkoxycarbonylamino, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkoxy, CHO, CO₂H, CO₂Na, CO₂NH₄, NR₉R₁₀, C(═O)NR₉R₁₀, OC(═O)NR₉R₁₀, C(═S)NR₉R₁₀ or SO₂NR₉R₁₀;

R₉ and R₁₀ may be the same or different, mutually independently selected from H, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₃-C₆ cycloalkyl or R₈;

(CHR₃)mCON(Q₂) links with phenyl ring at the 2, 3 or 4-position.

The preferred compounds of general formula (I) of this invention are:

R₁ is selected from H, C₁-C₆ alkyl, C₁-C₆haloalkyl, C₁-C₆cyanoalkyl, C₁-C₆alkoxyC₁-C₆alkyl, C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆haloalkoxycarbonyl, C₁-C₆alkylaminocarbonyl, C₁-C₆haloalkylaminocarbonyl, C₃-C₆cycloalkyl or R₈;

R₂ is selected from H, halogen, CN, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆cyanoalkoxy, C₁-C₆alkylthio, C₁-C₆alkoxyC₁-C₆alkyl, C₁-C₆haloalkoxyC₁-C₆alkyl, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₃-C₆cycloalkyl or R₈;

R₃ is selected from H or C₁-C₄alkyl; m is selected from 1 to 3;

R₄ is selected from halogen, CN, CONH₂, CSNH₂, NO₂, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkoxyC₁-C₄alkyl, C₁-C₄haloalkoxyC₁-C₄alkyl, C₁-C₄alkylthioC₁-C₄alkyl, C₁-C₄haloalkylthioC₁-C₄alkyl, C₁-C₄alkylamino, C₁-C₄haloalkylamino, C₂-C₄dialkylamino, piperidyl, Pyrrolidyl, N-methyl piperazinyl, morpholinyl, C₂-C₄alkenyl, C₂-C₄haloalkenyl, C₂-C₄alkenoxy, C₂-C₄haloalkenoxy, C₂-C₄alkynyl, C₂-C₄haloalkynyl, C₂-C₄alkynoxy, C₂-C₄haloalkynoxy, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl or R₈; n is selected from 0 to 3;

R₅ is selected from H, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxyC₁-C₄alkyl, C₃-C₆cycloalkyl, C₁-C₄cyanoalkyl, C₁-C₄alkylamino, C₁-C₄haloalkylamino, C₂-C₆dialkylamino, C₂-C₄alkenyl, C₂-C₄haloalkenyl, C₂-C₄alkynyl, C₂-C₄haloalkynyl, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfonyl, C₁-C₄alkylcarbonyl, C₁-C₄haloalkylcarbonyl, C₁-C₄alkyloxycarbonylC₁-C₄alkyl, C₁-C₄alkylcarbonylamino,

or R₈;

R₆ is selected from H, CN, SCN, H(C═O), C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylcarbonyl, C₁-C₄alkyloxycarbonyl, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄cyanoalkyl, C₁-C₄hydroxyalkyl, C₃-C₆cycloalkyl or R₈; p is selected from 0 to 4;

X₁ is selected from H, halogen, NO₂, CN, SCN, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄haloalkylthio, C₁-C₄alkoxyC₁-C₄alkyl, C₁-C₄haloalkoxyC₁-C₄alkyl, C₁-C₄alkylthioC₁-C₄alkyl or C₁-C₄haloalkylthioC₁-C₄alkyl;

X₂, X₃, X₄ and X₅ may be the same or different, mutually independently selected from H, halogen, CN, NO₂, OH, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio or C₁-C₄alkylsulfonyl;

Q₁ and Q₂ may be the same or different, mutually independently selected from H, NH₂, OH, CN, SCN, C₁-C₄cyanoalkyl, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkylcarbonyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkoxyC₁-C₄alkyl, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄alkylamino, C₂-C₆dialkylamino, piperidyl, Pyrrolidyl, N-methylpiperazinyl, morpholinyl, H(C═O), C₁-C₄alkylaminocarbonyl, C₁-C₄alkoxycarbonyl, C₁-C₄alkylaminothio, C₂-C₄dialkylaminothio, C₃-C₆cycloalkyl or R₈;

Y is selected from O, S or NR₇;

Z is O;

R₇ is selected from H, CN, NH₂, OH, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₃-C₆cycloalkyl, C₁-C₄cyanoalkyl, C₁-C₄cyanoalkoxy, C₁-C₄alkylamino, C₁-C₄haloalkylamino, C₂-C₄dialkylamino, piperidyl, pyrrolidyl, N-methylpiperazinyl, morpholinyl, 2,6-dimethylmorpholinyl, C₂-C₄alkenyl, C₂-C₄haloalkenyl, C₂-C₄alkenoxy, C₂-C₄haloalkenoxy, C₂-C₄alkynyl, C₂-C₄haloalkynyl, C₂-C₄alkynoxy, C₂-C₄haloalkynoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfonyl, C₁-C₄alkylcarbonyl, C₁-C₄haloalkylcarbonyl, C₁-C₄alkoxycarbonylC₁-C₄alkyl, C₁-C₄alkylcarbonylamino,

or R₈;

Or, when Y is selected from NR₇, NR₇ and R₅ form a unsubstituted or substituted five-membered or six-membered ring with 1-2 substitutents selected independently from C₁-C₃alkyl;

R₈ is selected from phenyl, benzoyl, phenoxycarbonyl, phenylaminocarbonyl, benzyl, phenethyl, naphthyl, pyridyl, picolyl, pyridylethyl, pyrimidyl, pyridazinyl, pyrazinyl, cyanuro, unsym-triazinyl, furanyl, thienyl, pyrrolyl, thiazolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadizolyl, benzofuryl, benzothiophenyl, benzothiazolyl, benzoxazolyl, benzoxazolylmethyl, benzopyranyl, benzopyronyl, benzopyridazinyl, indolyl, quinolyl, quinoxalinyl, triazolopyrimidinyl, imidazopyridinyl, imidazothiazolyl, purinyl, pyridylformoxyl, pyrimidinylformoxyl, pyridyloxycarbonyl, pyrimidinyloxycarbonyl, pyridylaminocarbonyl, pyrimidinylaminocarbonyl or thiazolylmethyl, which can be unsubstituted or further substituted with 1-3 substitutents, the substitutent(s) mentioned was (were) selected independently from halogen, NO₂, CN, SH, C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₆cycloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₂-C₄alkenyl, C₂-C₄haloalkenyl, C₂-C₄alkynyl, C₂-C₄haloalkynyl, C₃-C₆alkenoxy, C₃-C₆haloalkenoxy, C₃-C₆alkynoxy, C₃-C₆haloalkynoxy, C₁-C₄alkylsulfinyl, C₁-C₄haloalkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfonyl, C₁-C₄alkylcarbonyl, C₁-C₄haloalkylcarbonyl, C₁-C₄alkylcarbonyloxy, C₁-C₄alkylcarbonylamino, C₁-C₄alkylsulfonyloxy, C₁-C₄alkoxycarbonyl, C₁-C₄alkoxyC₁-C₄alkoxy, C₁-C₄alkoxycarbonylC₁-C₄alkyl, C₁-C₄alkoxycarbonylamino, C₁-C₄alkoxycarbonylC₁-C₄alkoxy, CHO, CO₂H, CO₂Na, CO₂NH₄, NR₉R₁₀, C(═O)NR₉R₁₀, OC(═O)NR₉R₁₀, C(═S)NR₉R₁₀ or SO₂NR₉R₁₀;

R₉ and R₁₀ may be the same or different, mutually independently selected from H, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₃-C₆cycloalkyl or R₈;

(CHR₃)mCON(Q₂) links with phenyl ring at the 2, 3 or 4-position.

Further more, the preferred compounds of general formula (I) of this invention are:

R₁ is selected from H, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxyC₁-C₄alkyl, C₃-C₆cycloalkyl or R;

R₂ is selected from H, chloride, bromine, fluorine, iodine, CN, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄cyanoalkoxy, C₁-C₄alkoxyC₁-C₄alkyl, C₁-C₄haloalkoxyC₁-C₄alkyl, C₃-C₆cycloalkyl or R₈;

R₃ is selected from H, methyl or ethyl; m is selected from 1, 2 or 3;

R₄ is selected from fluorine, chloride, bromine, iodine, CN, NO₂, C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylamino, C₂-C₄dialkylamino or C₁-C₃alkylsulfonyl; n is selected from 0, 1, 2 or 3;

R₅ is selected from H, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxyC₁-C₃alkyl, C₃-C₆cycloalkyl, C₁-C₄cyanoalkyl, C₁-C₄alkylamino, C₂-C₆dialkylamino, C₃-C₄alkenyl, C₃-C₄alkynyl or R₈;

R₆ is selected from H, CN, SCN, C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃alkylthio or C₁-C₃hydroxyalkyl; p is selected from 0, 1, 2 or 3;

X₁ is selected from H, fluorine, chloride, bromine, iodine, NO₂, CN, SCN, C₁-C₃alkyl or C₁-C₃haloalkyl;

X₂, X₃, X₄ and X₅ may be the same or different, mutually independently selected from H, fluorine, chloride, bromine, iodine, CN, NO₂, OH, C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy or C₁-C₃haloalkoxy;

Q₁ and Q₂ may be the same or different, mutually independently selected from H, CN, SCN, C₁-C₃alkyl, C₁-C₃alkylcarbonyl, C₁-C₃alkoxyC₁-C₂alkyl or H(C═O);

Y is selected from O or NR₇;

Z is O;

R₇ is selected from H, CN, NH₂, OH, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₃-C₆cycloalkyl, C₁-C₃cyanoalkyl, C₁-C₃cyanoalkoxy, C₁-C₃alkylamino, C₁-C₃haloalkylamino, C₂-C₄dialkylamino, piperidyl, pyrrolidyl, N-methylpiperazinyl, morpholinyl, 2,6-dimethylmorpholinyl, C₃-C₄alkenyl, C₃-C₄haloalkenyl, C₃-C₄alkenoxy, C₃-C₄haloalkenoxy, C₃-C₄alkynyl, C₃-C₄haloalkynyl, C₃-C₄alkynoxy, C₃-C₄haloalkynoxy, C₁-C₃alkylsulfonyl, C₁-C₃haloalkylsulfonyl or R;

Or, when Y is selected from NR₇, NR₇ and R₅ form piperidine, tetrahydropyrrole, N-methylpiperazine, morpholine or 2,6-dimethylmorpholine;

R is selected from phenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 4-methylphenyl, 4-trifluoromethylphenyl, 4-methoxylphenyl, 2,6-dichloro-4-trifluoromethylphenyl, benzoyl, 4-chlorobenzoyl, 2,4-dichlorobenzoyl, 4-trifluoromethylbenzoyl, phenoxycarbonyl, 4-chlorophenoxycarbonyl, 2,4-dichlorophenoxycarbonyl, 4-trifluoromethylphenoxycarbonyl, phenylaminocarbonyl, 4-chlorophenylaminocarbonyl, 2,4-dichlorophenylaminocarbonyl, 4-trifluoromethyphenylaminocarbonyl, benzyl, 4-chlorobenzyl, 4-tert-butylbenzyl, 4-trifluoromethylbenzyl, phenethyl, 2-pyridyl, 3-chloro-2-pyridyl, 3,5-dichloro-2-pyridyl, 3,5,6-trichloro-2-pyridyl, 5-trifluoromethyl-2-pyridyl, 5-methyl-2-pyridyl, 3-chloro-5-cyano-2-pyridyl, 3-chloro-5-trifluoromethyl-2-pyridyl, 2-picolyl, 2-chloro-5-picolyl, 3-chloro-5-trifluoro-2-picolyl, 2-pyridinylethyl, 3-chloro-5-trifluoromethyl-2-pyridinylethyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, thiazole-2-yl, 2-chloro-5-thiazolylmethyl, 3-pyridylformoxyl, 2-chloro-3-pyridylformoxyl, 2-chloro-5-pyridylformoxyl, 2-pyrimidinylformoxyl, 5-trifluoromethyl-2-pyrimidinylformoxyl, 2-pyridyloxycarbonyl, 3-chloro-2-pyridyloxycarbonyl, 3,5-dichloro-2-pyridyloxycarbonyl, 5-trifluoromethyl-2-pyridyloxycarbonyl, 5-methyl-2-pyridyloxycarbonyl, 3-chloro-5-cyano-2-pyridyloxycarbonyl, 3-chloro-5-trifluoromethyl-2-pyridyloxycarbonyl, 2-pyrimidinyloxycarbonyl, 5-trifluoromethyl-2-pyrimidinyloxycarbonyl, 2-pyridylaminocarbonyl, 3-chloro-2-pyridylaminocarbonyl or 2-pyrimidinylaminocarbonyl;

(CHR₃)mCON(Q₂) links with phenyl ring at the 2, 3 or 4-position.

Even more preferred compounds of formula (I) of this invention are:

R₁ is selected from H, methyl, ethyl, n-propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, trifluoromethyl, trifluoroethyl, methoxymethyl, ethoxymethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or R₈;

R₂ is selected from H, chloride, bromine, fluorine, CN, methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, trifluoromethyl, difluoromethyl, fluoromethyl, trifluoromethoxyl, trifluoroethoxyl, fluoromethoxyl, cyanomethoxyl, methoxymethyl, trifluoromethoxymethyl, trifluoroethoxymethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or R₈;

R₃ is selected from H or methyl; m is 1;

R₄ is selected from fluorine, chloride, bromine, iodine, CN, methyl, ethyl, trifluoromethyl, methoxyl, trifluoromethoxyl or methylsulfonyl; n is selected from 0, 1, 2 or 3;

R₅ is selected from H, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, trifluoromethyl, trifluoroethyl, cyclopropyl, cyclohexyl, cyanomethyl, allyl, propargyl or R₈;

R₆ is selected from H, CN, SCN, methyl or ethyl; p is selected from 0, 1, 2 or 3;

X₁ is selected from H, fluorine, chloride, bromine, iodine, NO₂, methyl or chloromethyl;

X₂, X₃, X₄ and X₅ may be the same or different, mutually independently selected from H, chloride, bromine or methoxyl;

Q₁ and Q₂ are H;

Y is selected from O or NR₇;

Z is O;

R₇ is selected from H, CN, NH₂, OH, methyl, ethyl, cyclopropyl, cyclopentyl, cyclohexyl, cyanomethyl, methylamino, dimethylamino, methylsulfonyl or R₈;

Or, when Y is selected from NR₇, NR₇ and R₅ form piperidine, tetrahydropyrrole, N-methylpiperazine, morpholine or 2,6-dimethylmorpholine;

R₈ is selected from phenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 4-methylphenyl, 4-trifluoromethylphenyl, 4-methoxylphenyl, 2,6-dichloro-4-trifluoromethylphenyl, benzyl, 4-chlorobenzyl, 4-tert-butylbenzyl, 4-trifluoromethylbenzyl, phenethyl, 2-pyridyl, 3-chloro-2-pyridyl, 3,5-dichloro-2-pyridyl, 3,5,6-trichloro-2-pyridyl, 5-trifluoromethyl-2-pyridyl, 5-methyl-2-pyridyl, 3-chloro-5-cyano-2-pyridyl, 3-chloro-5-trifluoromethyl-2-pyridyl, 2-picolyl, 2-chloro-5-picolyl, 3-chloro-5-trifluoromethyl-2-picolyl, 2-pyridinylethyl, 3-chloro-5-trifluoromethyl-2-pyridinylethyl, thiazole-2-yl, 2-chloro-5-thiazolylmethyl or 2-pyrimidinyl;

(CHR₃)mCON(Q₂) links with phenyl ring at the 2, 3 or 4-position.

Most preferred compounds of formula (I) of this invention are:

R₁ is selected from H, methyl, ethyl or 3-chloro-2-pyridyl;

R₂ is selected from bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, trifluoromethyl, cyclopropyl or 4-chlorophenyl;

R₃ is selected from H or methyl; m is 1;

R₄ is selected from fluorine, chloride, bromine, iodine, CN or methyl; n is selected from 0, 1 or 2;

R₆ is selected from H or methyl; p is selected from 0, 1, 2 or 3;

X₁ is selected from H, chloride or methyl;

X₂, X₃, X₄, X₅, Q₁, Q₂ are H;

Z is O;

YR₅ is selected from amino, methylamino, ethylamino, dimethylamino, methoxyl, ethoxyl or morpholinyl;

(CHR₃)mCON(Q₂) links with phenyl ring at the 2, 3 or 4-position.

In the compounds having the general formula (I) of the invention, due to chiral carbon or nitrogen connecting to different groups or substituents, which results in forming the stereoisomers (R and S respectively represents different configurations). Therefore, the compounds of the invention consist of R isomers, S isomers or any proportion of the mixture.

The following is the meaning of terms in the general formula (I):

Halogen or halo is fluorine, chlorine, bromine or iodine.

The “alkyl” stands for straight-chain or branched alkyl, such as methyl, ethyl, propyl, isopropyl, n-butyl or tert-butyl.

The “cycloalkyl” is substituted or unsubstituted cyclic alkyl, such as cyclopropyl, cyclopentyl or cyclohexyl. The substitute(s) is(are) methyl, halogen etc.

The “haloalkyl” stands for straight or branched chain alkyl, in which hydrogen atoms can be all or partly substituted with halogen, such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl etc.

The “cyanoalkyl” stands for straight or branched chain alkyl, in which hydrogen atoms can be all or partly substituted with cyano, such as —CH₂CN, —CH₂CH₂CN, —CH₂C(CH₃)₂CN, —CH₂CH(CN)₂ etc.

The “alkoxy” refers to straight or branched chain alkyl, which is linked to the structure by oxygen atom.

The “cyanoalkoxyl” refers to straight or branched chain cyanoalkyl, which is linked to the structure by oxygen atom, such as CNCH₂OO—.

The “alkoxyalkyl” refers to straight or branched chain alkoxyl, which is linked to the structure by alkyl, such as CH₃OCH₂—, CH₃CH₂OCH₂—.

The “haloalkoxyalkyl” refers to the alkyl of alkoxyalkyl, in which hydrogen atoms can be all or partly substituted with halogen, such as ClCH₂CH₂OCH₂—.

The “alkoxycarbonyl” means alkoxyl is linked to the structure by carbonyl. such as CH₃OCO—, CH₃CH₂OCO—.

The “alkoxycarbonylalkyl” means alkoxycarbonyl is linked to the structure by alkyl.

The “haloalkoxycarbonyl” stands for alkoxy of alkoxycarbonyl, in which hydrogen atoms can be all or partly substituted with halogen, such as ClCH₂CH₂OCO—.

The “haloalkoxy” refers to straight or branched chain alkoxy, in which hydrogen atoms may be all or partly substituted with halogen, such as chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, trifluoroethoxy etc.

The “alkylthio” refers to straight or branched chain alkyl, which is linked to the structure by sulfur atom.

The “alkylthioalkyl” refers to straight or branched chain alkylthio, which is linked to the structure by alkyl. such as CH₃SCH₂—.

The “haloalkylthio” refers to straight or branched chain alkylthio, in which hydrogen atoms may be all or partly substituted with halogen, such as chloromethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio etc.

The “haloalkylthioalkyl” means haloalkylthio is linked to the structure by alkyl.

The “alkylamino” means straight or branched chain alkyl is linked to the structure by Nitrogen atoms.

The “alkylaminothio”, such as CH₃NHS—, CH₃CH₂NHS—. The “alkylaminocarbonyl”, such as CH₃NHCO—, CH₃CH₂NHCO—.

The “haloalkylaminocarbonyl” refers to alkyl of alkylaminocarbonyl, in which hydrogen atoms may be all or partly substituted with halogen, such as CF₃NHCO—.

The “haloalkylamino” refers to straight or branched chain alkylamino, in which hydrogen atoms of alkyl may be all or partly substituted with halogen.

The “alkenyl” stands for a straight-chain or branched alkenes, such as vinyl, 1-propylene, 2-propylene or different butenyl, pentenyl or hexenyl isomers. Alkenyl also includes polyene, such as 1,2-propylene alkenyl and 2,4-the adipic alkenyl.

The “haloalkenyl” refers to a straight-chain or branched alkenes, in which hydrogen atoms may be all or partly substituted with halogen.

The “alkynyl” stands for a straight-chain or branched alkynes, such as acetenyl, 1-propargyl, 2-propargyl and different butynyl, pentynyl or hexynyl isomers. Alkynyl also includes group composed of many triple bonds, such as 2,5-hexadiynyl.

The “haloalkynyl” stands for a straight-chain or branched alkynes, in which hydrogen atoms may be all or partly substituted with halogen.

The “alkenoxyl” means straight or branched chain alkynes is linked to the structure by oxygen.

The “haloalkenoxyl” stands for a straight-chain or branched alkenoxyl, in which hydrogen atoms may be all or partly substituted with halogen.

The “alkynoxyl” means straight or branched chain alkynes is linked to the structure by oxygen.

The “haloalkynoxyl” stands for a straight-chain or branched alkynoxyl, in which hydrogen atoms may be all or partly substituted with halogen.

The “alkylcarbonyl” means alkyl is linked to the structure by carbonyl. such as CH₃CO—, CH₃CH₂CO—.

The “haloalkylcarbonyl” stands for a straight-chain or branched alkylcarbonyl, in which hydrogen atoms may be all or partly substituted with halogen, such as CF₃CO—.

The “alkylsulfinyl” means a straight-chain or branched alkyl is linked to the structure by (—SO—), such as methylsulfinyl.

The “haloalkylsulfinyl” stands for a straight-chain or branched alkylsulfinyl, in which hydrogen atoms may be all or partly substituted with halogen.

The “alkylsulfonyl” means a straight-chain or branched alkyl is linked to the structure by (—SO₂—), such as methylsulfonyl.

The “haloalkylsulfonyl” stands for a straight-chain or branched alkylsulfonyl, in which hydrogen atoms may be all or partly substituted with halogen.

The “phenoxycarbonyl” means phenoxy is linked to the structure by carbonyl, such as PhOCO—.

The “phenylaminocarbonyl” means phenylamino is linked to the structure by carbonyl, such as PhNHCO—.

The “phenylalkyl” means to phenyl is linked to the structure by alkyl, such as benzyl, phenethyl etc.

The “naphthylalkyl” means naphthyl is linked to the structure by alkyl, such as naphthalenemethyl, naphthaleneethyl etc.

The “heteroaryl” of the present invention refer to five-membered ring or six-membered ring containing 1 or more N, O, S heteroatoms, such as pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, furyl, thiazolyl, quinolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, pyrazolyl, pyranyl, triazolyl, tetrazyl, benzothiazolyl, benzofuryl etc. The “heteroarylcarbonyl” means heteroaryl is linked to the structure by carbonyl, such as pyridineformoxyl, pyrimidineformoxyl, pyrazolformoxyl. The “heteroaryloxycarbonyl” means heteroaryloxy is linked to the structure by carbonyl. The “heteroarylaminocarbonyl” means heteroarylamino is linked to the structure by carbonyl. The “heteroarylalkyl” means heteroaryl is linked to the structure by alkyl, such as furfuryl, pyridylethyl etc.

Detailed descriptions of the invention also provides a novel intermediate or its salt used to prepare the compounds of the general formula (I), their structures represented by the general formula (II):

Wherein:

R₃ is selected from H or C₁-C₁₂alkyl; m is selected from 0 to 5;

R₄ is selected from halogen, CN, CONH₂, CSNH₂, NO₂, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂haloalkoxyC₁-C₁₂alkyl, C₁-C₁₂alkylthioC₁-C₁₂alkyl, C₁-C₁₂haloalkylthioC₁-C₁₂alkyl, C₁-C₁₂alkylamino, C₁-C₁₂haloalkylamino, C₂-C₁₂dialkylamino, piperidyl, pyrrolidyl, N-methyl piperazinyl, morpholinyl, C₂-C₁₂alkenyl, C₂-C₁₂haloalkenyl, C₂-C₁₂alkenoxy, C₂-C₁₂haloalkenoxy, C₂-C₁₂alkynyl, C₂-C₁₂haloalkynyl, C₂-C₁₂alkynoxy, C₂-C₁₂haloalkynoxy, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl or R₈; n is selected from 0 to 4;

R₅ is selected from H, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₃-C₆cycloalkyl, C₁-C₁₂cyanoalkyl, C₁-C₁₂alkylamino, C₁-C₁₂haloalkylamino, C₂-C₁₂dialkylamino, C₂-C₁₂alkenyl, C₂-C₁₂haloalkenyl, C₂-C₁₂alkynyl, C₂-C₁₂haloalkynyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂haloalkylcarbonyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkylcarbonylamino,

or R₈;

R₆ is selected from H, CN, SCN, H(C═O), C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₁-C₁₂alkylcarbonyl, C₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂cyanoalkyl, C₁-C₁₂hydroxyalkyl, C₃-C₆cycloalkyl or R₈; p is selected from 0 to 5;

X₂, X₃, X₄ and X₅ may be the same or different, mutually independently selected from H, halogen, CN, NO₂, OH, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio or C₁-C₁₂alkylsulfonyl;

Q₁ and Q₂ may be the same or different, mutually independently selected from H, NH₂, OH, CN, SCN, C₁-C₁₂cyanoalkyl, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylsulfinyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₁₂alkylamino, C₂-C₁₂dialkylamino, piperidyl, pyrrolidyl, N-methyl piperazinyl, morpholinyl, H(C═O), C₁-C₁₂alkylaminocarbonyl, C₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, C₁-C₂alkylaminothio, C₂-C₁₂dialkylaminothio, C₃-C₆cycloalkyl or R₈;

Y is selected from O, S or NR₇;

Z is selected from O or S;

R₇ is selected from H, CN, NH₂, OH, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₃-C₆cycloalkyl, C₁-C₁₂cyanoalkyl, C₁-C₁₂cyanoalkoxy, C₁-C₁₂alkylamino, C₁-C₁₂haloalkylamino, C₂-C₁₂dialkylamino, piperidyl, Pyrrolidyl, N-methylpiperazinyl, morpholinyl, 2,6-dimethylmorpholinyl, C₂-C₁₂alkenyl, C₂-C₁₂haloalkenyl, C₂-C₁₂alkenoxy, C₂-C₁₂haloalkenoxy, C₂-C₁₂alkynyl, C₂-C₁₂haloalkynyl, C₂-C₁₂alkynoxy, C₂-C₁₂haloalkynoxy, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂haloalkylcarbonyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkylcarbonylamino,

or R₈;

Or, when Y is selected from NR₇, NR₇ and R₅ form a unsubstituted or substituted five-membered or six-membered ring with 1-4 substitutents selected independently from C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy or C₃-C₆cycloalkyl;

R₈ is selected from phenyl, benzoyl, phenoxycarbonyl, phenylaminocarbonyl, phenylC₁-C₆alkyl, naphthyl, naphthylC₁-C₆alkyl, heteroaryl, heteroarylcarbonyl, heteroaryloxycarbonyl, heteroarylaminocarbonyl or heteroarylC₁-C₆alkyl, which can be unsubstituted or further substituted with 1-5 substitutents, the substitutent(s) mentioned was (were) selected independently from halogen, NO₂, CN, SH, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₃-C₁₂cycloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₂-C₁₂alkenyl, C₂-C₁₂haloalkenyl, C₂-C₁₂alkynyl, C₂-C₁₂haloalkynyl, C₃-C₁₂alkenoxy, C₃-C₁₂haloalkenoxy, C₃-C₁₂alkynoxy, C₃-C₁₂haloalkynoxy, C₁-C₁₂alkylsulfinyl, C₁-C₁₂haloalkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂haloalkylcarbonyl, C₁-C₁₂alkylcarbonyloxy, C₁-C₁₂alkylcarbonylamino, C₁-C₂alkylsulfonyloxy, C₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkoxyC₁-C₁₂alkoxy, C₁-C₁₂ alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkoxycarbonylamino, C₁-C₁₂alkoxycarbonylC₁-C₂alkoxy, CHO, CO₂H, CO₂Na, CO₂NH₄, NR₉R₁₀, C(═O)NR₉R₁₀, OC(═O)NR₉R₁₀, C(═S)NR₉R₁₀ or SO₂NR₉R₁₀;

R₉ and R₁₀ may be the same or different, mutually independently selected from H, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₃-C₆ cycloalkyl or R₈;

(CHR₃)mCON(Q₂) links with phenyl ring at the 2, 3 or 4-position.

The acid that reacts with the amines of formula (II) to give the salts includes carboxylic acid, such as acetic acid, propionic acid, butyric acid, oxalic acid, adipic acid, dodecanedioic acid, lauric acid, stearic acid, trifluoroacetic acid, fumaric acid, maleic acid, benzoic acid or phthalic acid; sulfoacid such as methanesulfonic acid, 1,3-propanedisulfonic acid, p-toluenesulfonic acid or dodecylbenzenesulfonic acid; and inorganic acid, such as hydrochloric acid, sulfuric acid, nitric acid or carbonic acid, etc.

The compounds having general formula (I) of the invention can be prepared according to the following two schemes:

The compounds represented by general formula (I) were prepared by condensation reaction of intermediate amine compounds represented by general formula (II) with pyrazole carbonyl chloride represented by general formula (III) in proper solvents. The solvents mentioned may be selected from benzene, toluene, xylene, acetone, butanone, methylisobutylketone, tetrahydrofuran, acetonitrile, dioxane, N,N-Dimethylformamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, pyridine, methylene chloride, chloroform, dichloroethane, methyl acetate or ethyl acetate, etc.

The reaction above can be carried out in the presence or absence of base, the reaction is promoted in the presence of base. Proper base mentioned may be selected from alkali metal hydride such as sodium hydride; alkali metal hydroxides such as sodium hydroxide or potassium hydroxide; alkali metal carbonate such as sodium carbonate or potassium carbonate; organic amine such as pyridine or triethylamine.

The proper temperature mentioned is from room temperature to boiling point of the solvent, normal temperature is from 20 to 100° C.

The reaction time is in the range of 30 minutes to 20 hours, generally being 1-10 hours.

According to the scheme above:

The intermediate compounds represented by general formula (IV) and the compounds of the general formula (V) are allowed to react in the presence or absence of base in proper solvent to give the compounds of the general formula (VI); at the same time, the compounds of the general formula (VIII) are obtained by reacting the compounds of the general formula (III) and the compounds of the general formula (VII) under the same condition as the intermediate (VI); the preferred temperature is 0˜100° C.; the reaction time is in the range of 30 minutes to 20 hours, generally being 0.5-10 hours. proper solvent mentioned may be selected from N,N-dimethylformamide, dimethylsulfoxide, benzene, toluene, xylene, chloroform, methylene chloride, tetrahydrofuran, acetonitrile, dioxane or N-methyl-2-pyrrolidone, etc. Proper base mentioned when needed may be selected from alkali metal hydride such as sodium hydride; alkali metal hydroxides such as sodium hydroxide or potassium hydroxide; alkali carbonate such as sodium carbonate or potassium carbonate; organic amine such as pyridine or triethylamine.

Then the compounds represented by general formula (VIII) are reacted with the compounds of the general formula (VI) in the presence of base in proper solvent to give the compounds of the general formula (I); the preferred temperature is 0-160° C.; the reaction time is in the range of 30 minutes to 20 hours, generally being 0.5-10 hours. Proper base mentioned may be selected from alkali metal hydride such as sodium hydride; alkali metal hydroxides such as sodium hydroxide or potassium hydroxide; alkali carbonate such as sodium carbonate or potassium carbonate; organic amine such as pyridine or triethylamine. proper solvent mentioned may be selected from N,N-dimethylformamide, dimethylsulfoxide, benzene, toluene, xylene, chloroform, methylene chloride, tetrahydrofuran, acetonitrile, dioxane or N-methyl-2-pyrrolidone, etc. The detailed operation refers to the methods described in WO2007087906A.

Except for the detailed description about how to prepare the protected key intermediate represented by general formula (II), other materials and intermediates described above may be purchased or may be prepared according to the known methods, as shown in the following:

Substituted parazole carbonyl chloride represented by general formula (III) can be prepared according to the methods described in Bull. Soc. Chim. France, 293 (1996), U.S. Pat. No. 4,950,668, JP2292263, JP2053776, JP4069361 or JP4069379, etc. The materials represented by general formula (IV) are commercially available, wherein, L is a leaving group, selected from halogen, methyl methanesulfonate or p-toluenesulfonates; The materials represented by general formula (V) can be prepared according to the methods described in Kundiger D. G et al. J. Am. Chem. Soc. 1960, 82:2953; CN1827610 or Applied Chemical Industry 2010, 39 (9):1436-1442. The intermediates represented by general formula (VII) can be purchased or prepared according to the methods described in J. Am. Chem. Soc, 70, 3788 (1948), 82, 681 (1960), 82, 2386 (1960); Can. J. Chem, 49, 2990 (1971); J. Org. Chem, 37, 335 (1972) or Organic Syntheses, Coll. Vol. 3, p. 229, p. 720 (1955), Vol. 23, p. 71 (1943), Vol. 27, p. 18 (1947).

The key intermediate compounds of the general formula (I) (amine compounds represented by general formula (II)) can be prepared according to the following schemes:

When Q₁=H, the compounds of the general formula (II) can be prepared according to the following two schemes.

Firstly, in the general formula (II), when p=0 (namely substituted aniline analogs), the preparation methods are shown as follows:

According to the scheme above, the compounds of the general formula (X) are prepared by reacting di-tert-butyl dicarbonate with the compounds of the general formula (IX) at 0˜100° C. in proper solvent in the presence of proper base, the preferred temperature is 0˜50° C.; the reaction time is in the range of 30 minutes to 20 hours, generally being 0.5-10 hours. Proper solvent mentioned may be selected from benzene, toluene, xylene, chloroform, methylene chloride, THF, acetonitrile, dioxane, N,N-dimethylformamide, N-methyl-2-pyrrolidone or dimethylsulfoxide, etc; proper base mentioned may be selected from alkali carbonate such as sodium carbonate, sodium bicarbonate, potassium carbonate or potassium bicarbonate.

Then the compounds represented by general formula (X) and the compounds of the general formula (VI) are allowed to react in the presence of proper base in proper solvent to give the compounds of the general formula (XI); the preferred temperature is 0˜100° C.; the reaction time is in the range of 30 minutes to 20 hours, generally being 0.5-10 hours. Proper solvent mentioned may be selected from benzene, toluene, xylene, chloroform, methylene chloride, acetone, butanone, tetrahydrofuran, acetonitrile, dioxane, N,N-dimethylformamide, N-methyl-2-pyrrolidone or dimethylsulfoxide, etc; proper base mentioned may be selected from alkali metal hydride such as sodium hydride; alkali metal hydroxides such as sodium hydroxide or potassium hydroxide; alkali carbonate such as sodium carbonate or potassium carbonate; organic amine such as pyridine or triethylamine.

The compounds of the general formula (IIa) are obtained by deprotection of the compounds of the general formula (XI) in proper solvent in presence of proper acid to give corresponding salts and then alkalization. The preferred temperature is 0˜50° C.; the reaction time is in the range of 30 minutes to 20 hours, generally being 0.5-10 hours. Proper solvent mentioned may be selected from ethyl acetate, methyl acetate, methyl formate, benzene, toluene, xylene, chloroform, methylene chloride, water, tetrahydrofuran, acetonitrile, dioxane, N,N-dimethylformamide, N-methyl-2-pyrrolidone or dimethylsulfoxide, etc; proper acid mentioned may be selected from hydrochloric acid, trifluoroacetic acid, sulfuric acid, acetic acid, propionic acid, butyric acid, oxalic acid, adipic acid, dodecanedioic acid, lauric acid, stearic acid, fumaric acid, maleic acid, benzoic acid or phthalic acid, etc. proper base mentioned may be selected from alkali metal hydride such as sodium hydride; alkali metal hydroxides such as sodium hydroxide or potassium hydroxide; alkali carbonate such as sodium carbonate or potassium carbonate; organic amine such as pyridine or triethylamine. The preparation method in detail refers to patent WO2004093800A.

Secondly: in the general formula (II), when p is selected from 1 to 5, the preparation methods are shown as follows.

1. Reduction of Cyano:

The intermediate compounds represented by general formula (VI) and the compounds of the general formula (XII) are allowed to react in the presence of proper base in proper solvent to give the compounds of the general formula (XIII); the preferred temperature is 0˜100° C.; the reaction time is in the range of 30 minutes to 20 hours, generally being 0.5-10 hours. Proper solvent mentioned may be selected from benzene, toluene, xylene, chloroform, methylene chloride, acetone, butanone, tetrahydrofuran, acetonitrile, dioxane, N,N-dimethylformamide, N-methyl-2-pyrrolidone or dimethylsulfoxide, etc; proper base mentioned may be selected from alkali metal hydride such as sodium hydride; alkali metal hydroxides such as sodium hydroxide or potassium hydroxide; alkali carbonate such as sodium carbonate or potassium carbonate; organic amine such as pyridine or triethylamine.

Then the compounds represented by general formula (XIII) and hydrogen are allowed to react in the presence of a metal catalyst and aqueous ammonia in proper solvent at the temperature of 0˜100° C. to give the compounds of the general formula (IIb); the preferred temperature is 20˜50° C.; the reaction time is in the range of 30 minutes to 20 hours, generally being 0.5˜10 hours. Proper solvent mentioned may be selected from methanol, ethanol, isopropanol, benzene, toluene, xylene, acetone, butanone, methylisobutylketone, chloroform, methylene chloride, methyl acetate, ethyl acetate, tetrahydrofuran, dioxane, N,N-dimethylformamide, N-methyl-2-pyrrolidone or dimethylsulfoxide, etc. Metal catalysts mentioned may be selected from Raney-nickel, palladium carbon or platinum oxide, etc, which are known hydrogenation catalysts to the skilled person of this field. The preparation of the compounds refer to the methods described in J. Am. Chem. Soc, 70, 3788 (1948); 82, 681 (1960); 82, 2386 (1960): Can. J. Chem, 49, 2990 (1971): J. Org. Chem., 37, 335 (1972): Organic Syntheses, Coll. Vol. 3, p. 229, p. 720 (1955), Vol. 23, p. 71 (1943) or Vol. 27, p. 18 (1947).

2. Reduction of Oxime:

The method of how to obtain the compounds of general formula (IIc) by reaction of the compounds of the general formula (XIV) and hydrogen refers to that of how to obtain the compounds of general formula (IIb) by reacting the compounds of the general formula (XIII) and hydrogen mentioned above, such as reaction conditions, solvent, base and the choice of catalyst.

In the scheme above to prepare the intermediates of the general formula (II), Boc₂O represents di-tert-butyl dicarbonate. Other substituents have the same meanings as defined above. The sources of other intermediates are as follows: intermediates represented by general formula (IX) and (XII) can be purchased, the preparation of the intermediates represented by formula (XIV) refers to the known methods described in WO2001070671A, J. Am. Chem. Soc. 1960, 82:2953, Organic Syntheses, Coll. Vol. 7, p. 149 (1990) or Organic Syntheses, Vol. 64, p. 19 (1986), substituted aminobenzoic acid, halogenated acyl chloride and 4-hydroxy phenyl alkyl aldehyde or ketone are allowed to react to give corresponding phenyl alkyl aldehyde or ketone, which is(are) then reacted with hydroxylamine in the presence of base to give the compounds of the general formula (XIV).

when Q₁≠H, the compounds of the general formula (IId), (IIe) and (IIf) can be prepared according to the following schemes:

Wherein, hal is a leaving group, selected from halogen, methyl methanesulfonate or p-toluenesulfonates; Other groups are as defined above.

The detailed preparation refers to the methods described in WO2004093800A.

The intermediate compounds represented by general formula (IIa), (IIb) or (IIc) and di-tert-butyl dicarbonate are allowed to react in proper solvent to give the compounds of the general formula (IId); Detailed reaction condition refers to the method of how to prepare the compounds of general formula (X) from the compounds of the general formula (IX).

The compounds (IId) is then allowed to react with Q₁-hal in the presence of base in proper solvent at 0˜50° C. to give the compounds of the general formula (IIe). The preferred temperature is 0˜25° C.; the reaction time is in the range of 30 minutes to 20 hours, generally being 0.5-10 hours. The proper solvent mentioned may be selected from N,N-dimethylformamide, tetrahydrofuran, acetonitrile, dioxane and so on. The proper base mentioned may be selected from alkali metal hydride such as sodium hydride, alkali metal hydroxides such as sodium hydroxide or potassium hydroxide, alkali carbonate such as sodium carbonate or potassium carbonate, organic amine such as pyridine or triethylamine.

The compounds (IIf) are obtained by deprotection the compounds (IIe) in proper solvent in presence of proper acid to give corresponding salts and then alkalization. Detailed reaction condition refers to the preparation method to get (XI) from (IIa).

The amine salt of compounds represented by the general formula (II) can be prepared according to the following method.

The compounds (II) and proper acid are allowed to react in proper solvent at −5˜50° C. (The preferred temperature is 0˜25° C.) to give the amine salt according to the known methods disclosed in CN1511142A; Organic Syntheses, Coll. Vol. 4, p. 605 (1963) or Vol. 34, p. 64 (1954), etc., the proper acid mentioned may be selected from acetic acid, propionic acid, butyric acid, oxalic acid, adipic acid, dodecanedioic acid, lauric acid, stearic acid, trifluoroacetic acid, fumaric acid, maleic acid, benzoic acid, phthalic acid, methanesulfonic acid, 1,3-propylene sulfonic acid, p-toluenesulfonic acid, dodecylbenzenesulfonic acid, hydrochloric acid, sulfuric acid, nitric acid or carbonic acid, etc. the proper solvent mentioned may be selected from benzene, toluene, xylene, acetone, butanone, methylisobutylketone, chloroform, methylene chloride, tetrahydrofuran, acetonitrile, ethyl ether, methanol, ethanol, propanol, butanol or dioxane, etc.

To sum up, the technical scheme of the present invention includes a preferred process route of compounds having the general formula (I) (wherein Q₁=H, p=0-5), the synthetic scheme is shown as follows:

Each substituent in the reaction formula is as defined above except for special explanation.

In the general formula (I), (CHR₃)mCON(Q₂) links with phenyl ring respectively at the 2, 3 or 4-position.

When (CHR₃)mCON(Q₂) links with phenyl ring at the 2-position, the structure is shown by formula (I-1):

When (CHR₃)mCON(Q₂) links with phenyl ring at the 3-position, the structure is shown by formula (I-2):

When (CHR₃)mCON(Q₂) links with phenyl ring at the 4-position, the structure is shown by formula (I-3):

In the general formula (I), preferred substituents of R₁ refer to table 1; preferred substituents of R₂ refer to table 2; preferred substituents of (R₄)n respectively refer to table 3 (when (CHR₃)mCON(Q₂) links with phenyl ring at the 2-position.), table 4 (when (CHR₃)mCON(Q₂) links with phenyl ring at the 3-position.) and table 5 (when (CHR₃)mCON(Q₂) links with phenyl ring at the 4-position.), preferred substituents of Y—R₅ refer to table 6; preferred substituents of Qt and Q₂ refer to table 7; preferred substituents of X₂, X₃, X₄ and X₅ refer to table 8; other substituents are as defined above.

TABLE 1 Some of R₁ substituents —R₁ —R₁ —R₁ —R₁ —R₁ H CH₃ Et n-Pr i-Pr n-Bu i-Bu s-Bu t-Bu CF₃ CHF₂ CH₂CF₃ COCH₃ COEt CO-n-Pr CO-n-Bu CO-t-Bu CO₂CH₃ CO₂Et CO₂-n-Pr CO₂-i-Pr CH₂F CO₂-t-Bu CONHCH₃ CONHEt CONH-n-Pr CONH-i-Pr CONH-n-Bu CONH-i-Bu CONH-t-Bu CH₂CN CH₂OCH₃ COCF₃ CO₂CH₂CF₃ CONHCH₂CF₃

TABLE 2 Some of R₂ substituents —R₂ —R₂ —R₂ —R₂ —R₂ H F Cl Br CH₂CN CN CH₃ Et n-Pr i-Pr n-Bu i-Bu s-Bu t-Bu CF₃ OCH₃ OEt OCF₃ CHF₂ OCH₂CF₃ CH₂F OCH₂CN OCH₂F OCH₂CF₃ CH₂OCH₂CF₃ CH₂OCH₃ SCH₃ SEt SCH₂F CH₂SCH₃ SOCH₃ SOCF₃ SO₂CH₃ SO₂Et SO₂CH₂CF₃ SO₂CF₃

TABLE 3 Some of (R₄)n substituents of formula I-1 I-1

(R₄)n (R₄)n (R₄)n (R₄)n (R₄)n 3-Br 4-SCH₃ 4-SO₂CH₃ 4-CONH₂ 4-CSNH₂ 3-CH₃ 4-Br 5-OCH₃ 3-CH₃-5-NO₂ 6-CH₃-3,5-2Br 4-CH₃ 5-Br 3,5-2Cl 4-CH₃-3-NO₂ 3-OCF₃-4,6-2Cl 5-CH₃ 6-Br 3,5-2Br 4-CH₃-5-NO₂ 4-CH₃-5-NO₂- 3-Br 6-CH₃ 3-I 4-CH₃-5-Br 5-CH₃-3-NO₂ 3-CN-4,6-2Cl 3-Cl 4-I 6-CH₃-5-CN 6-CH₃-4-NO₂ 3-CN-4-CH₃- 6-Cl 4-Cl 5-I 3,5,6-3Cl 6-CH₃-5-NO₂ 3-CN-4-CF₃- 6-Cl 5-Cl 6-I 3-Et 3-NO₂-5-Cl 4-CH₃-5-CN- 6-Cl 6-Cl 3-CN 4-Et 3-NO₂-5-Br 4-CF₃-5-CN- 6-Cl 3-CF₃ 4-CN 5-Et 5-NO₂-3-Br 3-OCF₃-6-Cl 4-CF₃ 5-CN 6-Et 5-CH₃-3-Br 3-Cl-5-CN 5-CF₃ 6-CN 5-CF₃-3-Cl 6-CH₃-5-Br 5-CF₃-3,6-2Cl 6-CF₃ 3-NO₂ 5-CH₃-3-Cl 3-CF₃-6-Cl 3-Cl-5-CONH₂ 3-F 4-NO₂ 3-CH₃-5-I 3-CH₃-5-CN 3-Cl-5-CSNH₂ 4-F 5-NO₂ 3-CH₃-5-Cl 3,4,5-3Cl 3-CH₃-5-CSNH₂ 5-F 6-NO₂ 3-CH₃-5-Br 3,5,6-3 CH₃ 3-CH₃-5-CSNH₂ 6-F 6-OCH₃ 4,5,6-3Cl 5-CF₃-6-Cl 3-Cl-5-SO₂CH₃ 4,5-2Cl 4,5-2Br 3,5-2CH₃ 3-CN-6-Cl 3-CH₃-5- SO₂CH₃

TABLE 4 Some of (R₄)n substituents of formula I-2 I-2

(R₄)n (R₄)n (R₄)n (R₄)n (R₄)n 2-CH₃ 2-Br 6-OCH₃ 2-CH₃-5-NO₂ 6-CH₃-4,5-2Br 4-CH₃ 4-Br 5-OCH₃ 4-CH₃-6-NO₂ 5-OCF₃-4,6-2Cl 5-CH₃ 5-Br 2,5-2Cl 4-CH₃-5-NO₂ 4-CH₃-5-NO₂-6-Br 6-CH₃ 6-Br 2,5-2Br 5-CH₃-6-NO₂ 5-CN-4,6-2Cl 2-Cl 2-F 4-CH₃-5-Br 6-CH₃-4-NO₂ 5-CN-4-CH₃-6-Cl 4-Cl 4-F 6-CH₃-5-CN 6-CH₃-5-NO₂ 2-CN-4-CF₃-6-Cl 5-Cl 5-F 4,5,6-3Cl 2-NO₂-5-Cl 2-CH₃-5-CN-6-Cl 6-Cl 6-F 2-Et 4-NO₂-5-Br 4-CF₃-5-CN-6-Cl 2-CF₃ 2-CN 4-Et 5-NO₂-4-Br 2-OCF₃-6-Cl 4-CF₃ 4-CN 5-Et 5-CH₃-5-Br 5-CN-4-Cl 5-CF₃ 5-CN 6-Et 6-CH₃-4Br 5-CF₃-4,6-2Cl 6-CF₃ 6-CN 5-CF₃-6-Cl 4-CH₃-5-Br 5-CF₃-6-Cl 2-NO₂ 6-NO₂ 5-CH₃-4-Cl 4-CF₃-6-Cl 2-CN-6-Cl 4-NO₂ 2-I 4,5-2Cl 5-CH₃-2-Cl 4-CH₃-2-Cl 5-NO₂ 4-I 5-I 6-I 5,6-2CH₃

TABLE 5 Some of (R₄)n substituents of formula I-3 I-3

(R₄)n (R₄)n (R₄)n (R₄)n (R₄)n 2-F 2-i-Pr 2,6-2OCH₃ 2,3-2CH₃ 2-Cl-5-F 3-F 3-2-i-Pr 5,6-2OCH₃ 2,5-2CH₃ 2-Cl-5-Br 5-F 5-2-i-Pr 3,5-2OCH₃ 2,6-2CH₃ 2-Cl-54 6-F 6-2-i-Pr 3,6-2NO₂ 5,6-2CH₃ 3-Cl-54 2-Cl 2-CF₃ 3,5-2NO₂ 3,5-2CH₃ 5-Cl-2-Br 3-Cl 3-CF₃ 2,3-2NO₂ 3,6-2CH₃ 3,5,6-3F 5-Cl 5-CF₃ 5,6-2NO₂ 2,3-2 Et 2,3,6-3Cl 6-Cl 6-CF₃ 2,5-2NO₂ 5,6-2 Et 2,3,5-3Cl 2-Br 2-OCH₃ 2,6-2NO₂ 2,5-2 Et 2,3,6-3I 3-Br 3-OCH₃ 2,3-2CN 2,6-2 Et 3,5,6-3Cl 5-Br 5-OCH₃ 5,6-2CN 3,5-2 Et 2,5,6-3Cl 6-Br 6-OCH₃ 2,5-2CN 3,6-2Et 2,3,5-3Br 2-I 2-OCF₃ 2,6-2CN 2,3-2CF₃ 2,3,6-3Br 3-I 3-OCF₃ 3,5-2CN 3,6-2CF₃ 2,5,6-3Br 5-I 5-OCF₃ 3,6-2CN 3,5-2CF₃ 3,5,6-3Br 6-I 6-OCF₃ 2-F-5-Cl 5-CH₃-2-Br 5-CH₃-3-F 2-CN 2,3-2F 2-F-5-Br 5-CH₃-2-Cl 6-CH₃-3-Cl 3-CN 2,5-2F 2-F-5-I 2,5,6-3CH₃ 2-CH₃-3-Br 5-CN 5,6-2F 2-F-6-Cl 5-Et 2-CH₃-5-Br 6-CN 2,6-2F 3-CF₃-5-Cl 2,6-2Br 2-CH₃-3-F 2-NO₂ 3,6-2F 3,5,6-3F 6-CH₃-2-NO₂ 2-CH₃-3-Cl 3-NO₂ 3,5-2F 2,5-2OCF₃ 3,6-2Br 2-CH₃-5-F 5-NO₂ 2,3-2Cl 2-CH₃-3-NO₂ 2-CH₃-5-F 2-CH₃-5-Cl 6-NO₂ 2,5-2Cl 5-CH₃-2,6-2Br 2,5-2F-6-Cl 2-CH₃-6-Cl 2-CH₃ 5,6-2Cl 5-CH₃-2-F- 5-CF₃-2,6- 3-CH₃-2-Br 6-Cl 2Cl 3-CH₃ 2,6-2Cl 2-CN-5-Cl 5-CH₃-2-CN 3-CH₃-5-Cl 5-CH₃ 3,6-2Cl 2-CN-5-Br 3,5-2Br 3-CH₃-5-Br 6-CH₃ 3,5-2Cl 5-CN-2-CF₃ 3-CH₃-2,6- 3-CH₃-5-I 2Cl 2-Et₅ 2,3-2Br 5-CN-2-Cl 2-CH₃-3,6- 2-CH₃-5-I 2Br 3-Et 5,6-2Br 5-CN-2-NO₂ 2-F-5,6-2Br 2-CN-5,6- 2Cl 2,5-2Br 5-CH₃-2-F 5-F-2,6-2Br 5-CN-2,6-2Cl 6-Et

TABLE 6 Some of substituents of YR₅ —YR₅ —YR₅ —YR₅ —YR₅

NHCH₃ NHSO₂CH₃ NH-s-Bu ONHCH₃ NHEt NHCN NHCH₂-t-Bu ONHEt N(CH₃)₂ NHCH₂CN OCH₃ ON═C(CH₃)₂ N(Et)₂ NHOCH₃ OEt ON═C(CH₃)(Et) NHCF₃ NHOEt O-n-Pr ONHPh NHCH₂CF₃ NHPh O-i-Pr ON(CH₃)Ph N(CF₃)₂ NH-n-Pr O-n-Bu ON(CH₃)Ph-4-Cl NHNHCH₃ NH-n-Pr O-i-Bu ONH-n-Pr NHN(CH₃)₂ NH-n-Bu O-t-Bu ONH-i-Pr NHCONHPh NH-i-Bu OPh ONH-n-Bu NHNHCF₃ NH-t-Bu OCH₂Ph ONH-t-Bu NHNHCOCH₃ NHCO₂CH₃ O(CH₂)₂Ph OCH₂CO₂CH₃ O(CH₂)₂OCH₃ O(CH₂)₂OEt NHCH₂C═CH₂ NHN═C(CH₃)₂ OCH₂CN NHC(CH₃)₂CN

OCH₂C═CH₂ OC(CH₃)₂CN NHCH(CH₃)CN OCH₂CH₂O-n-Bu OCH₂Ph-4-Cl NHCH₂Ph NHCH₂Ph-4-Cl NH(CH₂)₂CN NH(CH₂)2Ph-4-Cl NHCH₂-2-Py OCH₂CF₃ NHCH₂-Ph-4-t-Bu ON═C(CH₃)Ph-4-Cl NHCH₂Ph-2,4-2Cl OCH₂Ph-2,4-2Cl NH(CH₂)₂Ph-4-t-Bu NHCH₂Ph-2,4-2OCH₃ OCH₂—Ph-4-t-Bu OCH₂Ph-4-OCH₃ O(CH₂)₂Ph-4-t-Bu OCH₂Ph-2,4-2OCH₃

TABLE 7 Some of substituents of Q₁ and Q₂ —Q₁(Q₂) —Q₁(Q₂) —Q₁(Q₂) —Q₁(Q₂) —Q₁(Q₂) H CN SCN OH NH2 CH₃ Et n-Pr i-Pr n-Bu i-Bu s-Bu t-Bu CF₃ CHF₂ CH₂CF₃ CH₂CN CH₂CH₂CN COCH₃ COEt CO-n-Pr CO-n-Bu CO-s-Bu CO-t-B OCH₃ OEt O-n-Pr O-i-Pr O-n-Bu O-i-Bu O-s-Bu O-t-Bu OCF₃ CH₂OCH₃ SOCH₃ SO₂CH₃ SO₂Et SO₂CF₃ SOCF₃ NHCH₃ NHEt N(CH₃)₂ N(Et)₂ HCO CONHCH₃ CONHEt COOCH₃ COOEt COO-n-Pr COO-i-Pr COO-n-Bu COO-s-Bu COO-t-Bu

TABLE 8 Some of substituents of X₂(X₃, X₄, X₅) in benzene —X₂ (X₃, —X₂ (X₃, —X₂ (X₃, —X₂ (X₃, —X₂ (X₃, X₄, X₅) X₄, X₅) X₄, X₅) X₄, X₅) X₄, X₅) H F Cl Br I CN NO₂ OH CH₃ Et n-Pr i-Pr n-Bu i-Bu s-Bu t-Bu CF₃ CHF₂ CH₂CF₃ OCH₃ OEt O—n-Pr O—i-Pr O—n-Bu O—i-Bu O—s-Bu O—t-Bu OCF₃ OCH₂CF₃ OCHF₂ SCH₃ SEt S—n-Pr S—i-Pr S—n-Bu S—i-Bu S—s-Bu S—t-Bu SO₂CH₃ SO₂Et

The preferred intermediates of general formula (II) are listed in table 9A and table 9B:

Table 9A Some of Intermediates of General Formula (II)

Wherein: Q₁ = Q₂ = X₂ = X₃ = X₄ = X₅ = H, Z = O, (CHR₃)mCON(Q₂) links with phenyl ring at the 2, 3 or 4-position; when (CHR₆)p = 0, Q₁—NH is connected with phenyl ring directly. N(Q₂) bonding melting point compound (CHR₃)m (R₄)n Y—R₅ (CHR₆)p position (° C.) II-1 CH₂ H NHCH₃ CH₂ 2 109-110 II-2 CH₂ H NHEt CH₂ 2 II-3 CH₂ H NH-i-Pr CH₂ 2 II-4 CH₂ H NH-t-Bu CH₂ 2 II-5 CH₂ H NHOH CH₂ 2 II-6 CH₂ H NHOCH₃ CH₂ 2 II-7 CH₂ H NHOEt CH₂ 2 II-8 CH₂ H ONHCH₃ CH₂ 2 II-9 CH₂ H NH₂ CH₂ 2 150-152 II-10 CH₂ H N(CH₃)₂ CH₂ 2 II-11 CH₂ H N(Et)₂ CH₂ 2 II-12 CH₂ H

CH₂ 2 II-13 CH₂ H

CH₂ 2 II-14 CH₂ H

CH₂ 2 185-186 II-15 CH₂ H

CH₂ 2 II-16 CH₂ H NHNH₂ CH₂ 2 II-17 CH₂ H NHCH₂CN CH₂ 2 II-18 CH₂ H NHC(CH₃)₂CN CH₂ 2 II-19 CH₂ H NHN(CH₃)₂ CH₂ 2 II-20 CH₂ H N(CH₃)NH₂ CH₂ 2 II-21 CH₂ H OCH₃ CH₂ 2 160-161 II-22 CH₂ H OEt CH₂ 2 II-23 CH₂ 3-CH₃ OCH₃ CH₂ 2 155-156 II-24 CH₂ H O(CH₂)₂OCH₃ CH₂ 2 II-25 CH₂ H OCH₂Ph CH₂ 2 II-26 CH₂ H OCH₂-5-Py-2-Cl CH₂ 2 II-27 CH₂ H N(CH₃)Ph CH₂ 2 II-28 CH₂ H NHCH₂Ph CH₂ 2 II-29 CH₂ H NHCH₂Ph-4-Cl CH₂ 2 II-30 CH₂ H NHCH₂Ph-4-OH-3-OCH₃ CH₂ 2 II-31 CH₂ H NHCH₂Ph-3,4-2OCH₃ CH₂ 2 II-32 CH₂ H NHCH₂-5-Py-2-Cl CH₂ 2 II-33 CH₂ H NH(CH₂) 2Ph-4-Cl CH₂ 2 II-34 CH₂ H NH(CH₂)2Ph-3,4-2OCH₃ CH₂ 2 II-35 CH₂ H NN═C(CH₃)₂ CH₂ 2 II-36 CH₂ 3-CH₃ NHCH₃ CH₂ 2 120-121 II-37 CH₂ 3-CH₃-5-Cl NHCH₃ CH₂ 2 II-38 CH₂ 3-CH₃-5-Br NHCH₃ CH₂ 2 97-99 II-39 CH₂ 3-CH₃-5-I NHCH₃ CH₂ 2 II-40 CH₂ 3-CH₃-5-CN NHCH₃ CH₂ 2 210-212 II-41 CH₂ 3-CH₃-5-CONH₂ NHCH₃ CH₂ 2 II-42 CH₂ 3-Cl NHCH₃ CH₂ 2 II-43 CH₂ 3,5-2Cl NHCH₃ CH₂ 2 II-44 CH₂ 3-Cl-5-Br NHCH₃ CH₂ 2 II-45 CH₂ 3-Cl-5-CN NHCH₃ CH₂ 2 II-46 CH₂ 3-Cl-5-CONH₂ NHCH₃ CH₂ 2 II-47 CH₂ 3-F NHCH₃ CH₂ 2 II-48 CH₂ 3-F-5-Cl NHCH₃ CH₂ 2 II-49 CH₂ 3-F-5-Br NHCH₃ CH₂ 2 II-50 CH₂ 3-F-5-CN NHCH₃ CH₂ 2 II-51 CH₂ 5-F NHCH₃ CH₂ 2 97-98 II-52 CH(CH₃) H NHCH₃ CH₂ 2 sticky liquid II-53 CH(CH₃) H NHEt CH₂ 2 II-54 CH(CH₃) H NH-i-Pr CH₂ 2 II-55 CH(CH₃) 3-CH₃ NHCH₃ CH₂ 2 II-56 CH(CH₃) 3-CH₃-5-Cl NHCH₃ CH₂ 2 II-57 CH(CH₃) 3-CH₃-5-Br NHCH₃ CH₂ 2 II-58 CH(CH₃) 3-CH₃-5-I NHCH₃ CH₂ 2 II-59 CH(CH₃) 3-CH₃-5-CN NHCH₃ CH₂ 2 II-60 CH(CH₃) 3-CH₃-5-CONH₂ NHCH₃ CH₂ 2 II-61 CH(CH₃) 3-Cl NHCH₃ CH₂ 2 II-62 CH(CH₃) 3,5-2Cl NHCH₃ CH₂ 2 II-63 CH(CH₃) 3-Cl-5-Br NHCH₃ CH₂ 2 II-64 CH(CH₃) 3-Cl-5-CN NHCH₃ CH₂ 2 II-65 CH(CH₃) 3-Cl-5-CONH₂ NHCH₃ CH₂ 2 II-66 CH(CH₃) 3-F NHCH₃ CH₂ 2 II-67 CH(CH₃) 3-F-5-Cl NHCH₃ CH₂ 2 II-68 CH(CH₃) 3-F-5-Br NHCH₃ CH₂ 2 II-69 CH(CH₃) 3-F-5-CN NHCH₃ CH₂ 2 II-70 CH(CH₃) 5-F NHCH₃ CH₂ 2 II-71 (CH₂)₂ H NHCH₃ CH₂ 2 89-90 II-72 (CH₂)₂ H NHEt CH₂ 2 II-73 (CH₂)₂ H NH-i-Pr CH₂ 2 II-74 (CH₂)₂ 3-CH₃ NHCH₃ CH₂ 2 II-75 (CH₂)₂ 3-CH₃-5-Cl NHCH₃ CH₂ 2 II-76 (CH₂)₂ 3-CH₃-5-Br NHCH₃ CH₂ 2 II-77 (CH₂)₂ 3-CH₃-5-I NHCH₃ CH₂ 2 II-78 (CH₂)₂ 3-CH₃-5-CN NHCH₃ CH₂ 2 II-79 (CH₂)₂ 3-CH₃-5-CONH₂ NHCH₃ CH₂ 2 II-80 (CH₂)₂ 3-Cl NHCH₃ CH₂ 2 II-81 (CH₂)₂ 3,5-2Cl NHCH₃ CH₂ 2 II-82 (CH₂)₂ 3-Cl-5-Br NHCH₃ CH₂ 2 II-83 (CH₂)₂ 3-Cl-5-CN NHCH₃ CH₂ 2 II-84 (CH₂)₂ 3-Cl-5-CONH₂ NHCH₃ CH₂ 2 II-85 (CH₂)₂ 3-F NHCH₃ CH₂ 2 II-86 (CH₂)₂ 3-F-5-Cl NHCH₃ CH₂ 2 II-87 (CH₂)₂ 3-F-5-Br NHCH₃ CH₂ 2 II-88 (CH₂)₂ 3-F-5-CN NHCH₃ CH₂ 2 II-89 (CH₂)₂ 5-F NHCH₃ CH₂ 2 II-90 CH₂ H NHCH₃ CH(CH₃) 2 II-91 CH₂ H NHEt CH(CH₃) 2 II-92 CH₂ H NH-i-Pr CH(CH₃) 2 II-93 CH₂ 3-CH₃ NHCH₃ CH(CH₃) 2 II-94 CH₂ 3-CH₃-5-Cl NHCH₃ CH(CH₃) 2 II-95 CH₂ 3-CH₃-5-Br NHCH₃ CH(CH₃) 2 II-96 CH₂ 3-CH₃-5-I NHCH₃ CH(CH₃) 2 II-97 CH₂ 3-CH₃-5-CN NHCH₃ CH(CH₃) 2 II-98 CH₂ 3-Cl NHCH₃ CH(CH₃) 2 II-99 CH₂ 3,5-2C1 NHCH₃ CH(CH₃) 2 II-100 CH₂ 3-C1-5-Br NHCH₃ CH(CH₃) 2 II-101 CH₂ 3-C1-5-CN NHCH₃ CH(CH₃) 2 II-102 CH₂ 3-F NHCH₃ CH(CH₃) 2 II-103 CH₂ 3-F-5-Cl NHCH₃ CH(CH₃) 2 II-104 CH₂ 3-F-5-Br NHCH₃ CH(CH₃) 2 II-105 CH₂ 3-F-5-CN NHCH₃ CH(CH₃) 2 II-106 CH₂ 5-F NHCH₃ CH(CH₃) 2 II-107 CH(CH₃) H NHCH₃ CH(CH₃) 2 II-108 CH(CH₃) H NHEt CH(CH₃) 2 II-109 CH(CH₃) H NH-i-Pr CH(CH₃) 2 II-110 CH(CH₃) 3-CH₃ NHCH₃ CH(CH₃) 2 II-111 CH(CH₃) 3-CH₃-5-Cl NHCH₃ CH(CH₃) 2 II-112 CH(CH₃) 3-CH₃-5-Br NHCH₃ CH(CH₃) 2 II-113 CH(CH₃) 3-CH₃-5-I NHCH₃ CH(CH₃) 2 II-114 CH(CH₃) 3-CH₃-5-CN NHCH₃ CH(CH₃) 2 II-115 CH(CH₃) 3-Cl NHCH₃ CH(CH₃) 2 II-116 CH(CH₃) 3,5-2Cl NHCH₃ CH(CH₃) 2 II-117 CH(CH₃) 3-Cl-5-Br NHCH₃ CH(CH₃) 2 II-118 CH(CH₃) 3-Cl-5-CN NHCH₃ CH(CH₃) 2 II-119 CH(CH₃) 3-F NHCH₃ CH(CH₃) 2 II-120 CH(CH₃) 3-F-5-Cl NHCH₃ CH(CH₃) 2 II-121 CH(CH₃) 3-F-5-Br NHCH₃ CH(CH₃) 2 II-122 CH(CH₃) 3-F-5-CN NHCH₃ CH(CH₃) 2 II-123 CH(CH₃) 5-F NHCH₃ CH(CH₃) 2 II-124 (CH₂)₂ H NHCH₃ CH(CH₃) 2 II-125 (CH₂)₂ H NHEt CH(CH₃) 2 II-126 (CH₂)₂ H NH-i-Pr CH(CH₃) 2 II-127 (CH₂)₂ 3-CH₃ NHCH₃ CH(CH₃) 2 II-128 (CH₂)₂ 3-CH₃-5-Cl NHCH₃ CH(CH₃) 2 II-129 (CH₂)₂ 3-CH₃-5-Br NHCH₃ CH(CH₃) 2 II-130 (CH₂)₂ 3-CH₃-5-I NHCH₃ CH(CH3) 2 II-131 (CH₂)₂ 3-CH₃-5-CN NHCH₃ CH(CH₃) 2 II-132 (CH₂)₂ 3-CH₃-5-CONH₂ NHCH₃ CH(CH₃) 2 II-133 (CH₂)₂ 3-Cl NHCH₃ CH(CH₃) 2 II-134 (CH₂)₂ 3,5-2Cl NHCH₃ CH(CH₃) 2 II-135 (CH₂)₂ 3-Cl-5-Br NHCH₃ CH(CH₃) 2 II-136 (CH₂)₂ 3-Cl-5-CN NHCH₃ CH(CH₃) 2 II-137 (CH₂)₂ 3-Cl-5-CONH₂ NHCH₃ CH(CH₃) 2 II-138 (CH₂)₂ 3-F NHCH₃ CH(CH₃) 2 II-139 (CH₂)₂ 3-F-5-Cl NHCH₃ CH(CH₃) 2 II-140 (CH₂)₂ 3-F-5-Br NHCH₃ CH(CH₃) 2 II-141 (CH₂)₂ 3-F-5-CN NHCH₃ CH(CH₃) 2 II-142 (CH₂)₂ 5-F NHCH₃ CH(CH₃) 2 II-143 CH₂ H NHCH₃ CH(CN) 2 II-144 (CH₂)₂ H NHCH₃ CH(CN) 2 II-145 CH(CH₃) H NHCH₃ CH(CN) 2 II-146 CH₂ H NHCH₃ (CH₂) 2 II-147 CH(CH₃) H NHCH₃ (CH₂) 2 II-148 (CH₂)₂ H NHCH₃ (CH₂) 2 II-149 CH₂ 3-CH₃ NHCH₃ (CH₂) 2 II-150 CH₂ 3-CH₃-5-Cl NIICH₃ (CH₂) 2 II-151 CH₂ 3-CH₃-5-Br NHCH₃ (CH₂) 2 II-152 CH₂ 3-CH₃-5-I NHCH₃ (CH₂) 2 II-153 CH₂ 3-CH₃₋5-CN NHCH₃ (CH₂) 2 II-154 CH₂ 3-CH₃-5-CONH₂ NHCH₃ (CH₂) 2 II-155 CH₂ 3-Cl NHCH₃ (CH₂) 2 II-156 CH₂ 3,5-2Cl NHCH₃ (CH₂) 2 II-157 CH₂ 3-Cl-5-Br NHCH₃ (CH₂) 2 II-158 CH₂ 3-Cl-5-CN NHCH₃ (CH₂) 2 II-159 CH₂ 3-Cl-5-CONH₂ NHCH₃ (CH₂) 2 II-160 CH₂ 3-F NHCH₃ (CH₂) 2 II-161 CH₂ 3-F-5-C1 NHCH₃ (CH₂) 2 II-162 CH₂ 3-F-5-Br NHCH₃ (CH₂) 2 II-163 CH₂ 3-F-5-CN NHCH₃ (CH₂) 2 II-164 CH₂ 5-F NHCH₃ (CH₂) 2 II-165 CH₂ H NHCH₃ CH₂ 3 II-166 CH₂ H NHCH₃ CH₂ 3 II-167 CH₂ H NHEt CH₂ 3 II-168 CH₂ H NH-i-Pr CH₂ 3 II-169 CH₂ H OCH₃ CH₂ 4 II-170 CH₂ H NHCH₃ CH₂ 4 II-171 CH₂ H NHEt CH₂ 4 II-172 CH₂ H NH-i-Pr CH₂ 4 II-173 CH₂ H NHCH₃ — 2 239-240 (hydrochloride) II-174 CH(CH₃) H NHCH₃ — 2 II-175 (CH₂)₂ H NHCH₃ — 2 II-176 CH₂ H OCH3 — 2 II-177 CH₂ H OEt — 2 II-178 CH₂ H o-i-Pr — 2 II-179 CH₂ H NHEt — 2 II-180 CH₂ 3-CH₃ NHCH₃ — 2 II-181 CH₂ 3-CH₃-5-Cl NHCH₃ — 2 II-182 CH₂ 3-CH₃-5-Br NHCH₃ — 2 II-183 CH₂ 3-CH₃-5-I NHCH₃ — 2 II-184 CH₂ 3-CH₃-5-CN NHCH₃ — 2 II-185 CH₂ 3-CH₃-5-CONH₂ NHCH₃ — 2 II-186 CH₂ 3-Cl NHCH₃ — 2 II-187 CH₂ H OEt CH₂ 4 138-139 “—” represents p = 0, namely chemical bond, means two groups were connected directly. ¹HNMR spectrum (¹HNMR, 300 MHz, internal standard: TMS, solvent CDCl₃) of some intermediates(II) in table 9A are shown as follows: II-1: δppm 3.73(3H, d), 3.81(2H, t), 5.18(2H, s), 7.02(2H, d), 7.24-7.27(3H, m), 7.51-7.52(1H, m), 7.72-7.77(2H, m), 8.28-8.31(1H, s). II-14: δppm 3.47(8H, s), 3.96(2H, s), 4.68(2H, d), 7.02(2H, d), 7.20(1H, t), 7.29-7.32(1H, m), 7.90(1H, d), 8.39(1H, s), 9.96(1H, s). II-38: δppm 3.25(3H, s), 3.60(3H, s), 3.66(2H, s), 5.22(2H, s), 6.99(2H, d), 7.23(2H, d), 7.77(1H, s), 8.03(1H, s). II-40: δppm 2.62(3H, s), 3.74(3H, s), 3.82(2H, s), 5.21(2H, s), 7.03(2H, d), 7.76(1H, s), 8.45(1H, s). II-52: δppm 1.57(3H, d), 1.80-1.84(1H, m), 3.73(3H, d), 5.18-5.23(2H, m), 7.00(1H, d), 7.06-7.09(2H, m), 7.24-7.31(2H, m), 7.50-7.54(1H, m), 7.71-7.75(2H, m), 8.26-8.30(1H, m). II-173: δppm 3.82(3H, s), 5.31(2H, s), 7.18(2H, d), 7.38(2H, d), 7.53(1H, t), 7.70-7.79 (2H, m), 8.13-8.16(1H, m),10.43(3H, s). II-187: δppm 1.39(3H, t), 1.95-1.99(2H, m), 4.37(2H, t), 4.59(2H, s), 6.84(2H, d), 7.21(2H, d), 7.69(2H, d), 8.02(1H, s), 8.58(1H, s).

TABLE 9B Some of intermediates of general formula (II)

Wherein: X₂ = X₄ = R₃ = H, Z = O, m = 1, n = 0 namely (R₄)n = H, (CHR₃)mCON(Q₂) links with phenyl ring at the 2-position; compound Q₁ Q₂ X₃ X₅ Y—R₅ (CHR₆)p II-188 H H H Cl NHCH₃ CH₂ II-189 H H H Cl NHEt CH₂ II-190 H H H CI NH-i-Pr CH₂ II-191 H H H Cl NH-t-Bu CH₂ II-192 H H H CI NHOH CH₂ II-193 H H H Cl NHOCH₃ CH₂ II-194 H H H Cl NHOEt CH₂ II-195 H H H Cl ONHCH₃ CH₂ II-196 H H H Cl NH₂ CH₂ II-197 H H H Cl N(CH₃)₂ CH₂ II-198 H H H Cl N(Et)₂ CH₂ II-199 H H H Cl

CH₂ II-200 H H H Cl

CH₂ II-201 H H H Cl

CH₂ II-202 H H H Cl

CH₂ II-203 H H H Cl NHNH₂ CH₂ II-204 H H H Cl NHCH₂CN CH₂ II-205 H H H Cl NHC(CH₃)₂CN CH₂ II-206 H H H Cl NHN(CH₃)₂ CH₂ II-207 H H H Cl N(CH₃)NH₂ CH₂ II-208 H H H Cl OCH₃ CH₂ II-209 H H H Cl OEt CH₂ II-210 H H H Cl O-i-Pr CH₂ II-211 H H H Cl O(CH₂)₂OCH₃ CH₂ II-212 H H H Cl OCH₂Ph CH₂ II-213 H H H Cl OCH₂-5-Py-2-Cl CH₂ II-214 H H H Cl N(CH₃)Ph CH₂ II-215 H H H Cl NHCH₂Ph CH₂ II-216 H H H Cl NHCH₂Ph-4-Cl CH₂ II-217 H H H Cl NHCH₂Ph-4-OH-3-OCH₃ CH₂ II-218 H H H Cl NHCH₂Ph-3,4-2OCH₃ CH₂ II-219 H H H Cl NHCH₂-5-Py-2-Cl CH₂ II-220 H H H Cl NH(CH₂)2Ph-4-Cl CH₂ II-221 H H H Cl NH(CH₂)2Ph-3,4-2OCH₃ CH₂ II-222 H H H Cl NN═C(CH₃)₂ CH₂ II-223 H H H Br NHCH₃ CH₂ II-224 H H H Br NHEt CH₂ II-225 H H H Br NH-i-Pr CH₂ II-226 H H H OEt NHCH₃ CH₂ II-227 H H H OEt NHEt CH₂ II-228 H H H OEt NH-i-Pr CH₂ II-229 H H H OEt NHCH₃ CH₂ II-230 H H H OEt NHEt CH₂ II-231 H H H OEt NH-i-Pr CH₂ II-232 H H Cl Cl NHCH₃ CH₂ II-233 H H Cl Cl NHEt CH₂ II-234 H H Cl Cl NH-i-Pr CH₂ II-235 H H Cl Br NHCH₃ CH₂ II-236 H H Cl Br NHEt CH₂ II-237 H H Cl Br NH-i-Pr CH₂ II-238 H H Cl OCH₃ NHCH3 CH₂ II-239 H H Cl OCH₃ NHEt CH₂ II-240 H H Cl OCH₃ NH-i-Pr CH₂ II-241 H H H Cl NHCH₃ CH(CH₃) II-242 H H H Br NHCH₃ CH(CH₃) II-243 H H H OCH₃ NHCH₃ CH(CH₃) II-244 H H Cl Cl NHCH₃ CH(CH₃) II-245 H H Cl Br NHCH₃ CH(CH₃) II-246 H H Cl OCH₃ NHCH₃ CH(CH₃) II-247 H H H Cl NHCH₃ CH(CN) II-248 H H H Br NHCH₃ CH(CN) II-249 H H H OCH₃ NHCH₃ CH(CN) II-250 H H Cl Cl NHCH₃ CH(CN) II-251 H H Cl Br NHCH₃ CH(CN) II-252 H H Cl OCH₃ NHCH₃ CH(CN) II-253 H H H Cl NHCH₃ CH₂CH₂ II-254 H H H Br NHCH₃ CH₂CH₂ II-255 H H H OCH₃ NHCH₃ CH₂CH₂ II-256 H H Cl Cl NHCH₃ CH₂CH₂ II-257 H H Cl Br NHCH₃ CH₂CH₂ II-258 H H Cl OCH₃ NHCH₃ CH₂CH₂ II-259 CN H H Cl NHCH₃ CH₂ II-260 CN H H Br NHCH₃ CH₂ II-261 CN H H OCH₃ NHCH₃ CH₂ II-262 CN H Cl Cl NHCH₃ CH₂ II-263 CN H Cl Br NHCH₃ CH₂ II-264 CN H Cl OCH₃ NHCH₃ CH₂ II-265 H CH₃ H Cl NHCH₃ CH₂ II-266 H CH₃ H Br NHCH₃ CH₂ II-267 H CH₃ H OCH₃ NHCH₃ CH₂ II-268 H CH₃ Cl Cl NHCH₃ CH₂ II-269 H CH₃ Cl Br NHCH₃ CH₂ II-270 H CH₃ Cl OCH₃ NHCH₃ CH₂

Some of intermediates (VI) are presented in table 10.

TABLE 10

In formula (VI), L = Cl, Z = O, (CHR₃)mCON(Q₂) links with phenyl ring at the 2, 3 or 4-position; N(Q₂) melting Bonding point compound (CHR₃)m Q₂ (R₄)n Y—R₅ position (° C.) VI-1 CH₂ H H NHCH₃ 2 155-157 VI-2 CH₂ H H NHEt 2 VI-3 CH₂ H H NH-i-Pr 2 VI-4 CH₂ H H NH-t-Bu 2 VI-5 CH₂ H H NHOH 2 VI-6 CH₂ H H NHOCH₃ 2 VI-7 CH₂ H H NHOEt 2 VI-8 CH₂ H H ONHCH₃ 2 VI-9 CH₂ H H NH₂ 2 175-176 VI-10 CH₂ H H N(CH₃)₂ 2 115-116 VI-11 CH₂ H H N(Et)₂ 2 VI-12 CH₂ H H

2 VI-13 CH₂ H H

2 VI-14 CH₂ H H

2 VI-15 CH₂ H H

2 VI-16 CH₂ H H NHNH₂ 2 VI-17 CH₂ H H NHNHCH₃ 2 VI-18 CH₂ H H NHN(CH₃)₂ 2 VI-19 CH₂ H H N(CH₃)NH₂ 2 VI-20 CH₂ H H OCH₃ 2 92-94 VI-21 CH₂ H H OEt 2 VI-22 CH₂ H H O-i-Pr 2 VI-23 CH₂ H H O(CH₂)₂OCH₃ 2 VI-24 CH₂ H H OCH₂Ph 2 VI-25 CH₂ H H OCH₂-5-Py-2-Cl 2 VI-26 CH₂ H H N(CH₃)Ph 2 VI-27 CH₂ H H NHCH₂Ph 2 VI-28 CH₂ H H NHCH₂Ph-4-Cl 2 VI-29 CH₂ H H NHCH₂Ph-4-OH-3-OCH₃ 2 VI-30 CH₂ H H NHCH₂Ph-3,4-2OCH₃ 2 VI-31 CH₂ H H NHCH₂-5-Py-2-Cl 2 VI-32 CH₂ H H NH(CH₂)2Ph-4-Cl 2 VI-33 CH₂ H H NH(CH₂)2Ph-3,4-2OCH₃ 2 VI-34 CH₂ H H NN═C(CH₃)2 2 VI-33 CH₂ H H NHCH₂CN 2 VI-34 CH₂ H H NHC(CH₃)₂CN 2 VI-35 CH₂ H 3-CH₃ NHCH₃ 2 195-196 VI-36 CH₂ H 3-CH₃-5-Cl NHCH₃ 2 >250 VI-37 CH₂ H 3-CH₃-5-Br NHCH₃ 2 201-202 VI-38 CH₂ H 3-CH₃-5-I NHCH₃ 2 VI-39 CH₂ H 3-CH₃-5-CN NHCH₃ 2 221-222 VI-40 CH₂ H 3-CH₃-5-CONH₂ NHCH₃ 2 VI-41 CH₂ H 3-Cl NHCH₃ 2 VI-42 CH₂ H 3,5-2Cl NHCH₃ 2 VI-43 CH₂ H 3-Cl-5-Br NHCH₃ 2 VI-44 CH₂ H 3-Cl-5-CN NHCH₃ 2 VI-45 CH₂ H 3-Cl-5-CONH₂ NHCH₃ 2 VI-46 CH₂ H 3-F NHCH₃ 2 VI-47 CH₂ H 3-F-5-Cl NHCH₃ 2 VI-48 CH₂ H 3-F-5-Br NHCH₃ 2 VI-49 CH₂ H 3-F-5-CN NHCH₃ 2 VI-50 CH₂ H 5-F NHCH₃ 2 VI-51 CH₂ CH₃ H NHCH₃ 2 VI-52 CH₂ CH₃ H OCH₃ 2 VI-53 CH₂ CH₃ H OEt 2 VI-54 CH(CH₃) H H NHCH₃ 2 121-122 VI-56 CH(CH₃) H H OCH₃ 2 63-65° C. VI-57 CH(CH₃) H H OEt 2 VI-58 CH(CH₃) CH₃ H NHCH₃ 2 VI-59 CH(CH₃) CH₃ H OCH₃ 2 VI-60 (CH₂)₂ H H NHCH₃ 2 VI-61 (CH₂)₂ H H OCH₃ 2 VI-62 CH₂ H H NHCH₃ 3 190-191 VI-63 CH₂ H H OCH₃ 3 VI-64 CH(CH₃) H H NHCH₃ 3 VI-65 CH(CH₃) H H OCH₃ 3 VI-66 (CH₂)₂ H H NHCH₃ 3 VI-67 (CH₂)₂ H H OCH₃ 3 VI-68 CH₂ H H NHCH₃ 4 VI-69 CH₂ H H OCH₃ 4 VI-70 CH(CH₃) H H NHCH₃ 4 VI-71 CH(CH₃) H H OCH₃ 4 VI-72 (CH2)₂ H H NHCH₃ 4 VI-73 (CH₂)₂ H H OCH₃ 4 VI-74 (CH₂)₃ H H NHCH₃ 2 98-99 VI-75 CH₂ H H OEt 4 106-107 VI-76 CH₂ H 5-Cl OCH₃ 2 217-218 VI-77 CH₂ H 3-CH₃ NHEt 2 119-120 VI-78 CH₂ H 3-CH₃ N(CH₃)₂ 2 209-210 VI-79 CH₃ H H OEt 2 150-152 ¹HNMR spectrum (¹HNMR, 300 MHz, internal standard: TMS, solvent CDCl₃) of some intermediates(VI) in table 10 are shown as follows: VI-1: δppm 3.02(3H, s), 4.18(2H, s), 6.36(1H, s), 7.11-7.16(1H, m), 7.47-7.52(2H, m), 8.57(1H, d), 11.91(1H, s). VI-35: δppm 2.36(3H, s), 2.94(3H, d), 4.17(2H, s), 6.21(1H, s), 7.16-7.21(1H, m), 7.27-7.35(1H, m), 9.69(1H, s). VI-37: δppm 2.16(3H, s), 2.70(3H, d), 4.23(2H, s), 7.45(1H, d), 7.56-7.57(1H, d), 8.25(1H, d), 9.86(1H, s). VI-39: δppm 2.26(3H, s), 2.74(3H, d), 4.26(2H, s), 7.31(1H, s), 7.82(1H, s), 8.37(1H, d), 10.16(1H, s). VI-56: δppm 1.83(3H, d), 3.96(3H, s), 4.50-4.61(1H, m), 7.14(1H, t), 7.53-7.60(1H, m), 8.03-8.09(1H, m), 8.70(1H, d), 11.81(1H, s). VI-62: δppm 3.02(3H, d), 4.21(2H, s), 6.19(1H, s), 7.42(1H, t), 7.55(1H, d), 7.74(1H, d), 7.96(1H, s), 8.36(1H, s). VI-75: δppm 1.39(3H, t), 4.22(2H, s), 4.36-4.38(2H,m), 7.65(2H, d), 8.04(2H, d), 8.40(1H, s). VI-79: δppm 1.40(3H, t), 4.22(2H, s), 4.36-4.43(2H,m), 7.45(1H, t), 7.86(1H, d), 7.95(1H, d), 8.04-8.05(1H, m), 8.39(1H, s).

Some of intermediates (VIII) are presented in table 11.

TABLE 11

physical compound R₁ R₂ X₁ Q₁ X₃ X₅ (CHR₆)p property/° C. VIII-1 CH₃ CH₃ Cl H H H CH₂ 131-133 VIII-2 CH₃ Et Cl H H H CH₂ 167-168 VIII-3 CH₃ n-Pr Cl H H H CH₂ VIII-4 CH₃ i -Pr Cl H H H CH₂ VIII-5 CH₃ t -Bu Cl H H H CH₂ VIII-6 CH₃

Cl H H H CH₂ VIII-7 CH₃ CF₃ C H H H CH₂ VIII-8 CH₃ CH₂OCH₃ CI H H H CH₂ VIII-9 CH₃ CH₂OCH₂CF₃ Cl H H H CH₂ VIII-10 CH₃ CH₂Cl Cl H H H CH₂ VIII-11 CH₃ CH₂CN Cl H H H CH₂ VIII-12 CH₃ Cl Cl H H H CH₂ VIII-13 CH₃ Br Cl H H H CH₂ VIII-14 CH₃ OCF₃ Cl H H H CH₂ VIII-15 CH₃ OCH₂CF₃ Cl H H H CH₂ VIII-16 CH₃ OCH₂CN Cl H H H CH₂ VIII-17 CH₃ Ph Cl H H H CH₂ VIII-18 CH₃ Ph-4-Cl Cl H H H CH₂ VIII-19 CH₃ Ph-2,4-2Cl Cl H H H CH₂ VIII-20 CH₃ Ph-4-CH₃ Cl H H H CH₂ VIII-21 CH₃ Ph-2,4-2CH₃ Cl H H H CH₂ VIII-22 CH₃ Ph-4-CF₃ Cl H H H CH₂ VIII-23 CH₃ Ph-4-OCF₃Cl H H H CH₂ CH₂ VIII-24 CH₃ 3-Py-2-Cl Cl H H H CH₂ VIII-25 CH₃ 2-Py-5-Cl Cl H H H CH₂ VIII-26 CH₃ 3-Py Cl H H H CH₂ VIII-27 CH₃ CH₃ H H H H CH₂ VIII-28 CH₃ Et H H H H CH₂ VIII-29 CH₃ n-Pr H H H H CH₂ VIII-30 CH₃ i -Pr H H H H CH₂ VIII-31 CH₃ t -Bu H H H H CH₂ VIII-32 CH₃

H H H H CH₂ VIII-33 CH₃ CF₃ H H H H CH₂ VIII-34 CH₃ CH₃ Br H H H CH₂ VIII-35 CH₃ Et Br H H H CH₂ VIII-36 CH₃ n-Pr Br H H H CH₂ VIII-37 CH₃ i -Pr Br H H H CH₂ VIII-38 CH₃ t -Bu Br H H H CH₂ VIII-39 CH₃

Br H H H CH₂ VIII-40 CH₃ CF₃ Br H H H CH₂ VIII-41 Et CH₃ H H H H CH₂ VIII-42 Et Et H H H H CH₂ VIII-43 Et n-Pr H H H H CH₂ VIII-44 Et i -Pr H H H H CH₂ VIII-45 Et t -Bu H H H H CH₂ VIII-46 Et

H H H H CH₂ VIII-47 Et CF₃ H H H H CH₂ VIII-48 Et CH₃ Cl H H H CH₂ VIII-49 Et Et Cl H H H CH₂ VIII-50 Et Pr Cl H H H CH₂ VIII-51 Et i -Pr Cl H H H CH₂ VIII-52 Et t -Bu Cl H H H CH₂ VIII-53 Et

Cl H H H CH₂ VIII-54 Et CF₃ CI H H H CH₂ VIII-55 i -Pr CH₃ CI H H H CH₂ VIII-56 i -Pr CH₃ H H H H CH₂ VIII-57

CH₃ Cl H H H CH₂ VIII-58

CH₃ H H H H CH₂ VIII-59 CH₂CF₃ CH₃ Cl H H H CH₂ VIII-60 CH₂CF₃ CH₃ H H H H CH₂ VIII-61 Ph CH₃ Cl H H H CH₂ VIII-62 Ph CH₃ H H H H CH₂ VIII-63 Ph Cl H H H H CH₂ VIII-64 Ph Br H H H H CH₂ VIII-65 Ph-2-Cl CH₃ Cl H H H CH₂ VIII-66 Ph-2-Cl CH₃ H H H H CH₂ VIII-67 Ph-2-Cl Cl H H H H CH₂ VIII-68 Ph-2-Cl Br H H H H CH₂ VIII-69 Ph-4-Cl CH₃ Cl H H H CH₂ VIII-70 Ph-4-Cl CH₃ H H H H CH₂ VIII-71 Ph-4-Cl Cl H H H H CH₂ VIII-72 Ph-4-Cl Br H H H H CH₂ VIII-73 2-Py-3-Cl CH₃ Cl H H H CH₂ VIII-74 2-Py-3-Cl CH₃ H H H H CH₂ VIII-75 2-Py-3-Cl Cl H H H H CH₂ VIII-76 2-Py-3-Cl Br H H H H CH₂ VIII-77 2-Py-3-Cl CF₃ H H H H CH₂ VIII-78 2-Py-3-Cl CHF₂ H H H H CH₂ VIII-79 2-Py-3-Cl OCF₃ H H H H CH₂ VIII-80 2-Py-3-Cl OCH₂CF₃ H H H H CH₂ VIII-81 2-Py-3-Cl OCH₂CN H H H H CH₂ VIII-82 2-Py-3-Cl OCH₂F H H H H CH₂ VIII-83 2-Py-3,5-2Cl Cl H H H H CH₂ VIII-84 2-Py-3,5-2Cl Br H H H H CH₂ VIII-85 2-Py-3,5,6-3Cl Cl H H H H CH₂ VIII-86 2-Py-3,5,6-3Cl Br H H H H CH₂ VIII-87 2-Py-3-Cl-5-CF₃Cl H H H H CH₂ CH₂ VIII-88 2-Py-3-Cl-5-CF₃Br H H H H CH₂ CH₂ VIII-89 2-Py-5-CF₃ Cl H H H H CH₂ VIII-90 2-Py-5-CF₃ Br H H H H CH₂ VIII-91 2-Py-3-Cl-5-CH₃ Cl H H H H CH₂ VIII-92 2-Py-3-Cl-5-CH₃ Br H H H H CH₂ VIII-93 CH₃ CH₃ Cl CH₃ H H CH₂ VIII-94 CH₃ Et Cl CH₃ H H CH₂ VIII-95 CH₃ CF₃ Cl CH₃ H H CH₂ VIII-96 CH₃ CH₃ Cl CN H H CH₂ VIII-97 CH₃ Et Cl CN H H CH₂ VIII-98 CH₃ CF₃ Cl CN H H CH₂ VIII-99 CH₃ CH₃ Cl H H Cl CH₂ VIII-100 CH₃ Et Cl H H Cl CH₂ VIII-101 CH₃ CF₃ Cl H H Cl CH₂ VIII-102 CH₃ CH₃ Cl H H Br CH₂ VIII-103 CH₃ Et Cl H H Br CH₂ VIII-104 CH₃ CF₃ Cl H H Br CH₂ VIII-105 CH₃ CH₃ Cl H H OCH₃ CH₂ VIII-106 CH₃ Et Cl H H OCH₃ CH₂ VIII-107 CH₃ CF₃ Cl H H OCH₃ CH₂ VIII-108 CH₃ CH₃ Cl H Cl Cl CH₂ VIII-109 CH₃ Et Cl H Cl Cl CH₂ VIII-110 CH₃ CF₃ C H Cl Cl CH₂ VIII-111 CH₃ CH₃ Cl H Cl OCH₃ CH₂ VIII-112 CH₃ Et Cl H Cl OCH₃ CH₂ VIII-113 CH₃ CF₃ Cl H Cl OCH₃ CH₂ VIII-114 Et CH₃ Cl H H Cl CH₂ VIII-115 Et CH₃ Cl H H Br CH₂ VIII-116 Et CH₃ Cl H H OCH₃ CH₂ VIII-117 Ph CH₃ Cl H H OCH₃ CH₂ VIII-118 Ph-2-Cl CH₃ Cl H H OCH₃ CH₂ VIII-119 Ph-4-Cl CH₃ Cl H H OCH₃ CH₂ VIII-120 2-Py-3-Cl Cl H H H OCH₃ CH₂ VIII-121 2-Py-3,5-2Cl Cl H H H OCH₃ CH₂ VIII-122 2-Py-3,5,6-3Cl Cl H H H OCH₃ CH₂ VIII-123 2-Py-3-Cl-5-CF₃ Cl H H H OCH₃ CH₂ VIII-124 2-Py-5-CF₃ Cl H H H OCH₃ CH₂ VIII-125 2-Py-3-Cl-5-CH₃ Cl H H H OCH₃ CH₂ VIII-126 CH₃ CH₃ Cl H H H CH₂(CH₃) VIII-127 CH₃ Et Cl H H H CH₂(CH₃) VIII-128 CH₃ CF₃ Cl H H H CH₂(CH₃) VIII-129 CH₃ CH₃ H H H H CH₂(CH₃) VIII-130 CH₃ Et H H H H CH₂(CH₃) VIII-131 CH₃ CF₃ H H H H CH₂(CH₃) VIII-132 CH₃ CH₃ Cl H H H CH₂(CN) VIII-133 CH₃ Et Cl H H H CH₂(CN) VIII-134 CH₃ CF₃ Cl H H H CH₂(CN) VIII-135 CH₃ CH₃ H H H H CH₂(CN) VIII-136 CH₃ Et H H H H CH₂(CN) VIII-137 CH₃ CF₃ H H H H CH₂(CN) VIII-138 CH₃ CH₃ Cl H H H (CH₂)₂ 157-159 VIII-139 CH₃ Et Cl H H H (CH₂)₂ 170-171 VIII-140 CH₃ CF₃ Cl H H H (CH₂)₂ VIII-141 Et CH₃ Cl H H H (CH₂)₂ VIII-142 Et Et Cl H H H (CH₂)₂ VIII-143 Et CF₃ Cl H H H (CH₂)₂ VIII-144 CH₃ CH₃ H H H OCH₃ CH₂ VIII-145 CH₃ Et H H H OCH₃ CH₂ VIII-146 CH₃ CF₃ H H H OCH₃ CH₂ VIII-147 Et CH₃ H H H OCH₃ CH₂ VIII-148 Ph CH₃ H H H OCH₃ CH₂ VIII-149 CH₃ CH₃ H H H OCH₃ (CH₂)₂ VIII-150 Et CH₃ H H H OCH₃ (CH₂)₂ ¹HNMR spectrum (¹HNMR, 300 MHz, internal standard: TMS, solvent CDCl₃) of some intermediates in table 11 are shown as follows: VIII-1: δppm 2.23(3H, s), 4.14(3H, s), 4.56(2H, d), 5.25(1H, s), 6.82(2H, d), 7.24(2H, d). VIII-2: δppm 1.23(3H, t), 2.62-2.64(2H, m), 4.14(3H, s), 4.56(2H, d), 5.21(1H, s), 6.82(2H, d), 7.23(2H, d). VIII-138: δppm 1.62(3H, s), 2.85(2H, t), 3.60-3.75 (2H, m), 4.10(3H, s), 5.33(1H, s), 6.72(1H, s), 6.80(2H, d), 7.10(2H, d). VIII-139: δppm 7.22(3H, t), 2.55-2.67(2H, m), 2.86(2H, t), 3.60-3.76(2H, m), 4.11(3H, s), 6.74(1H, s), 6.79(2H, d), 7.10(2H, d).

The present invention are also explained by the following compounds listed in tables 12-17, but without being restricted thereby.

TABLE 12 Some of compounds of formula I-1 I-1

(Q₁, Q₂, X₂, X₃, X₄, X₅ = H, Z = O) No. R₁ R₂ (CHR₃)m (R₄)n X₁ Y—R₅ (CHR₆)p  1 CH₃ Cl CH₂ H H NHCH₃ CH₂  2 CH₃ CH₃ CH₂ H H NHCH₃ CH₂  3 CH₃ Et CH₂ H H NHCH₃ CH₂  4 CH₃ n-Pr CH₂ H H NHCH₃ CH₂  5 CH₃ i-Pr CH₂ H H NHCH₃ CH₂  6 CH₃ n-Bu CH₂ H H NHCH₃ CH₂  7 CH₃ i-Bu CH₂ H H NHCH₃ CH₂  8 CH₃

CH₂ H Cl NHCH₃ CH₂  9 CH₃ t-Bu CH₂ H H NHCH₃ CH₂  10 CH₃ CF₃ CH₂ H H NHCH₃ CH₂  11 CH₃ OCH₃ CH₂ H H NHCH₃ CH₂  12 CH₃ OEt CH₂ H H NHCH₃ CH₂  13 CH₃ Ph CH₂ H H NHCH₃ CH₂  14 CH₃ Ph-4-Cl CH₂ H H NHCH₃ CH₂  15 CH₃ CH₃ CH₂ H Cl NHCH₃ CH₂  16 CH₃ Et CH₂ H Cl NHCH₃ CH₂  17 CH₃ n-Pr CH₂ H Cl NHCH₃ CH₂  18 CH₃ i-Pr CH₂ H Cl NHCH₃ CH₂  19 CH₃ n-Bu CH₂ H Cl NHCH₃ CH₂  20 CH₃ i-Bu CH₂ H Cl NHCH₃ CH₂  21 CH₃ s-Bu CH₂ H Cl NHCH₃ CH₂  22 CH₃ t-Bu CH₂ H Cl NHCH₃ CH₂  23 CH₃ CF₃ CH₂ H Cl NHCH₃ CH₂  24 CH₃ OCH₃ CH₂ H Cl NHCH₃ CH₂  25 CH₃ Ph-4-Cl CH₂ H Cl NHCH₃ CH₂  26 CH₃ CH₃ CH₂ H Br NHCH₃ CH₂  27 CH₃ Et CH₂ H Br NHOCH₃ CH₂  28 CH₃ n-Pr CH₂ H Br NHNHCH₃ CH₂  29 CH₃ OCH₂F CH₂ H Br NHCH₃ CH₂  30 CH₃ OCH₂CF₃ CH₂ H Cl NHCH₃ CH₂  31 CH₃ Ph-4-Cl CH₂ H Br NHCH₃ CH₂  32 CH₃ CH₃ CH₂ H NO₂ NHCH₃ CH₂  33 CH₃ Et CH₂ H NO₂ NHCH₃ CH₂  34 CH₃ n-Pr CH₂ H NO₂ NHCH₃ CH₂  35 CH₃ i-Pr CH₂ H NO₂ NHCH₃ CH₂  36 CH₃ Et CH₂ H NO₂ NHCH₃ CH₂  37 CH₃ CF₃ CH₂ H NO₂ NHCH₃ CH₂  38 CH₃ OCF₃ CH₂ H NO₂ NHCH₃ CH₂  39 CH₃ Ph-4-Cl CH₂ H NO₂ NHCH₃ CH₂  40 CH₃ CH₃ CH(CH₃) H CH₃ NHCH₃ CH₂  41 CH₃ Et CH₂ H Cl NHCH₃ R-*CH(CH₃)  42 CH₃ CF₃ CH₂ H CH₃ NHCH₃ CH₂  43 CH₃ Ph CH₂ H CH₃ NHCH₃ CH₂  44 CH₃ Ph-4-Cl CH₂ H CH₃ NHCH₃ CH₂  45 CH₃ CH₃ CH₂ H CN NHCH₃ CH₂  46 CH₃ Et CH₂ H Cl NHCH₃ S-*CH(CH₃)  47 CH₃ CF₃ CH₂ H CN NHCH₃ CH₂  48 CH₃ OCH₃ CH₂ H CN NHCH₃ CH₂  49 CH₃ Ph-4-Cl CH₂ H CN NHCH₃ CH₂  50 CH₃ CH₃ CH₂ H SO₂CF₃ NHCH₃ CH₂  51 CH₃ Et CH₂ H SO₂CF₃ NHCH₃ CH₂  52 CH₃ CF₃ CH₂ H SO₂CF₃ NHCH₃ CH₂  53 CH₃ Ph-4-Cl CH₂ H SO₂CF₃ NHCH₃ CH₂  54 CH₃ CH₃ CH₂ H SOCF₃ NHCH₃ CH₂  55 CH₃ Et CH₂ H SOCF₃ NHCH₃ CH₂  56 CH₃ CF₃ CH₂ H SOCF₃ NHCH₃ CH₂  57 CH₃ Ph-4-Cl CH₂ H SOCF₃ NHCH₃ CH₂  58 CH₃ CH₃ CH₂ H OCH₃ NHCH₃ CH₂  59 CH₃ CF₃ CH₂ H OCH₃ NHCH₃ CH₂  60 CH₃ Ph-4-Cl CH₂ H OCH₃ NHCH₃ CH₂  61 CH₃ CH₃ CH(CH₃) H H NHCH₃ CH₂  62 CH₃ Et CH(CH₃) H Cl NHCH₃ (CH₂)₂  63 CH₃ OCH₃ CH(CH₃) H H NHCH₃ CH₂  64 CH₃ Ph-4-Cl CH(CH₃) H H NHCH₃ CH₂  65 CH₃ CH₃ CH(CH₃) H Cl NHCH₃ CH₂  66 CH₃ Et R-*CH(CH₃) H Cl NHCH₃ CH₂  67 CH₃ n-Pr CH(CH₃) H Cl NHCH₃ CH₂  68 CH₃ i-Pr CH(CH₃) H Cl NHCH₃ CH₂  69 CH₃ Et S-*CH(CH₃) H Cl NHCH₃ CH₂  70 CH₃ CF₃ CH(CH₃) H Cl NHCH₃ CH₂  71 CH₃ Ph-4-Cl CH(CH₃) H Cl NHCH₃ CH₂  72 CH₃ CH₃ CH(CH₃) H Br NHCH₃ CH₂  73 CH₃ Et CH(CH₃) H Br NHCH₃ CH₂  74 CH₃ CH₃ CH(CH₃) H NO₂ NHCH₃ CH₂  75 CH₃ Et CH(CH₃) H NO₂ NHCH₃ CH₂  76 CH₃ CF₃ CH(CH₃) H NO₂ NHCH₃ CH₂  77 CH₃ CH₃ CH₂ H CH₃ NHCH₃ CH₂  78 CH₃ CH₃ CH(CH₃) H Cl NHCH₃ (CH₂)₂  79 CH₃ CF₃ CH(CH₃) H CH₃ NHCH₃ CH₂  80 CH₃ CH₃ (CH₂)₂ H H NHCH₃ CH₂  81 CH₃ CH₃ (CH₂)₂ H Cl NHCH₃ CH₂  82 CH₃ Et (CH₂)₂ H H NHCH₃ CH₂  83 CH₃ Et (CH₂)₂ H Cl NHCH₃ CH₂  84 CH₃ CH₃ (CH₂)₃ H H NHCH₃ CH₂  85 CH₃ CH₃ (CH₂)₃ H Cl NHCH₃ CH₂  86 CH₃ Et (CH₂)₃ H H NHCH₃ CH₂  87 CH₃ Et (CH₂)₃ H Cl NHCH₃ CH₂  88 CH₃ CH₃ CH₂ H H OCH₃ CH₂  89 CH₃ Et CH₂ H H OCH₃ CH₂  90 CH₃ n-Pr CH₂ H H OCH₃ CH₂  91 CH₃ i-Pr CH₂ H H OCH₃ CH₂  92 CH₃ i-Bu CH₂ H H OCH₃ CH₂  93 H CF₃ CH₂ H H OCH₃ CH₂  94 CH₃ CH₃ CH₂ 3-CH₃ Cl OEt CH₂  95 CH₃ CH₃ CH₂ H Cl OEt CH₂  96 CH₃ n-Pr CH₂ H Cl OCH₃ CH₂  97 CH₃ i-Pr CH₂ H Cl OCH₃ CH₂  98 CH₃ i-Bu CH₂ H Cl OCH₃ CH₂  99 CH₃ Et CH₂ H Cl OEt CH₂ 100 CH₃ t-Bu CH₂ H Cl OCH₃ CH₂ 101 CH₃ CF₃ CH₂ H Cl OCH₃ CH₂ 102 CH₃ OCH₃ CH₂ H Cl OCH₃ CH₂ 103 CH₃ Ph CH₂ H Cl OCH₃ CH₂ 104 Et CH₃ CH₂ H H NHCH₃ CH₂ 105 Et Et CH₂ H H NHCH₃ CH₂ 106 Et CF₃ CH₂ H H OCH₃ CH₂ 107 Et CH₃ CH₂ H Cl NHCH₃ CH₂ 108 Et Et CH₂ H Cl NHCH₃ CH₂ 109 Et n-Pr CH₂ H Cl OCH₃ CH₂ 110 Et i-Pr CH₂ H Cl OCH₃ CH₂ 111 Et CF₃ CH₂ H Cl NHOCH₃ CH₂ 112 2-Py-3-Cl CH₃ CH₂ H H NHCH₃ CH₂ 113 2-Py-3-Cl CF₃ CH₂ H H NHCH₃ CH₂ 114 2-Py-3-Cl Cl CH₂ H H NHCH₃ CH₂ 115 2-Py-3-Cl OCH₂CF₃ CH₂ H H NHCH₃ CH₂ 116 2-Py-3-Cl OCH₂CN CH₂ H H NHCH₃ CH₂ 117 2-Py-3-Cl Br CH₂ H H NHCH₃ CH₂ 118 2-Py-3-Cl Br CH₂ 3-CH₃-5-CN H NHCH₃ CH₂ 119 2-Py-3-Cl OCH₂F CH₂ H H NHCH₃ CH₂ 120 2-Py-3,5-2Cl CF₃ CH₂ H H NHCH₃ CH₂ 121 2-Py-3-Cl Br CH₂ 3-CH₃-5-Br H NHCH₃ CH₂ 122 2-Py-3,5-2Cl CH₃ CH₂ H H NHCH₃ CH₂ 123 2-Py-3,5-2Cl Br CH₂ H H NHCH₃ CH₂ 124 2-Py-3-Cl-5-CF₃ Br CH₂ H H NHCH₃ CH₂ 125 2-Py-3-Cl-5-CH₃ CH₃ CH₂ H H NHCH₃ CH₂ 126 2-Py-3-Cl-5-CF₃ CH₃ CH₂ H H NHCH₃ CH₂ 127 2-Py-5-CF₃ CH₃ CH₂ H H NHCH₃ CH₂ 128 2-Py-5-CF₃ Cl CH₂ H H NHCH₃ CH₂ 129 H CF₃ CH₂ H H NHCH₃ CH₂ 130 H CH₃ CH₂ H Cl NHCH₃ CH₂ 131 H Et CH₂ H Cl NHCH₃ CH₂ 132 H CF₃ CH₂ H Cl NHCH₃ CH₂ 133 CH₃ CH₃ CH₂ H H NHEt CH₂ 134 CH₃ Et CH₂ H H NHEt CH₂ 135 CH₃ OCH₂CF₃ CH₂ H H NHCH₃ CH₂ 136 CH₃ CH₂OCH₃ CH₂ H H NHCH₃ CH₂ 137 CH₃ CF₃ CH₂ H H NHEt CH₂ 138 CH₃ CH₃ CH₂ H Cl NHEt CH₂ 139 CH₃ Et CH₂ H Cl NHEt CH₂ 140 CH₃ OCH₂CN CH₂ H Cl NHCH₃ CH₂ 141 CH₃ Et CH₂ 5-F Cl NHEt CH₂ 142 CH₃ CF₃ CH₂ H Cl NHEt CH₂ 143 CH₃ CH₃ CH₂ H H N(CH₃)₂ CH₂ 144 CH₃ Et CH₂ H H N(CH₃)₂ CH₂ 145 CH₃ n-Pr CH₂ H H N(CH₃)₂ CH₂ 146 CH₃ CF₃ CH₂ H H N(CH₃)₂ CH₂ 147 CH₃ CH₃ CH₂ H Cl N(CH₃)₂ CH₂ 148 CH₃ Et CH₂ H Cl N(CH₃)₂ CH₂ 149 CH₃ i-Pr CH₂ H Cl N(CH₃)₂ CH₂ 150 CH₃ CF₃ CH₂ H Cl N(CH₃)₂ CH₂ 151 CH₃ CH₃ CH₂ H H NH₂ CH₂ 152 CH₃ Et CH₂ H H NH₂ CH₂ 153 CH₃ n-Pr CH₂ 3-CH₃-4-CN H NH₂ CH₂ 154 CH₃ 3-Py CH₂ H H NH₂ CH₂ 155 CH₃ CF₃ CH₂ H H NH₂ CH₂ 156 CH₃ CH₃ CH₂ H Cl NH₂ CH₂ 157 CH₃ Et CH₂ H Cl NH₂ CH₂ 158 CH₃ n-Pr CH₂ 2-CH₃-5-I Cl NH₂ CH₂ 159 CH₃ i-Pr CH₂ H Cl NH₂ CH₂ 160 CH₃ CF₃ CH₂ H Cl NH₂ CH₂ 161 CH₃ CH₃ CH₂ 5-Cl H NHCH₃ CH₂ 162 CH₃ CH₃ CH₂ 3-CH₃-5-I Cl NHCH₃ CH₂ 163 CH₃ CH₃ CH₂ 3-CH₃-5-Cl H NHCH₃ CH₂ 164 CH₃ CH₃ CH₂ 3-CH₃ H NHCH₃ CH₂ 165 CH₃ CH₃ CH₂ 5-Br H NHCH₃ CH₂ 166 CH₃ CH₃ CH₂ 3-CH₃-5-Br Cl NHCH₃ CH₂ 167 CH₃ CH₃ CH₂ 3-CH₃-5-CN Cl NHCH₃ CH₂ 168 CH₃ CH₃ CH₂ 3,5-2Cl H NHCH₃ CH₂ 169 CH₃ CH₃ CH₂ 5-F H NHCH₃ CH₂ 170 CH₃ Et CH₂ 3-CH₃ Cl NHCH₃ CH₂ 171 CH₃ CH₃ CH₂ 3-CH₃ Cl NHCH₃ CH₂ 172 CH₃ Et CH₂ 3-CH₃-5-Cl Cl NHCH₃ CH₂ 173 Ph CH₃ CH₂ H Cl NHCH₃ CH₂ 174 Ph-4-Cl CH₃ CH₂ H Cl NHCH₃ CH₂ 175 Ph CH₃ CH₂ H H NHCH₃ (CH₂)₃ 176 Ph-4-Cl CH₃ CH₂ H H NHCH₃ (CH₂)₃ 177 CH₃ CH₃ CH₂ 3-CH₃ H NHEt CH₂ 178 CH₃ Et CH₂ 3-CH₃ Cl OEt CH₂ 179 CH₃ CH₃ CH₂ 5-F H NHEt CH₂ 180 CH₃ CH₃ CH₂ 3-CH₃-5-CN H NHCH₃ CH₂ 181 CH₃ Et CH₂ 3-CH₃-5-Br Cl NHCH₃ CH₂ 182 CH₃ CH₃ CH₂ 3-CH₃-5-Cl Cl NHCH₃ CH₂ 183 CH₃ Et CH₂ 3,5-2Cl Cl NHCH₃ CH₂ 184 CH₃ CH₃ CH₂ 5-CH₃-3-Cl H NHEt CH₂ 185 CH₃ Et CH₂ 3-CN-5-CH₃ Cl OEt CH₂ 186 CH₃ CH₃ CH₂ H Cl NHCH₃ (CH₂)₂ 187 CH₃ Et CH₂ H Cl NHCH₃ (CH₂)₂ 188 CH₃ CH₃ CH₂ 5-F H NHCH₃ (CH₂)₂ 189 2-Py-3-Cl Br CH₂ 3-CH₃-5-Cl H NHCH₃ CH₂ 190 CH₃ Et CH₂ 3-CH₃-5-CN H NHCH₃ CH₂ 191 2-Py-3-Cl Br CH₂ 3,5-2Cl H NHCH₃ CH₂ 192 2-Py-3-Cl CH₃ CH₂ 3-CH₃ H NHCH₃ CH₂ 193 CH₃ Et CH₂ 3-CH₃-5-CN Cl NHCH₃ CH₂ 194 CH₃ CH₃ CH₂ H Cl NHCH₃ (CH₂)₃ 195 CH₃ CH₃ CH₂ H Cl

CH₂ 196 CH₃ CH₃ CH₂ H H

CH₂ 197 CH₃ Et CH₂ H H

CH₂ 198 CH₃ CH₃ CH₂ H Cl

CH₂ 199 CH₃ CH₃ CH₂ H CH₃ NHCH₃ (CH₂)₃ 200 CH₃ CH₃ CH₂ H Cl N(CH₃)₂ — 201 CH₃ Et CH₂ H Cl N(CH₃)₂ — 202 CH₃ CH₃ CH₂ H Cl NHCH₃ — 203 CH₃ Et CH₂ H Cl N(CH₃)₂ — 204 CH₃ CH₃ CH₂ 3-CH₃-5-Cl Cl N(CH₃)₂ CH₂ 205 CH₃ Et CH₂ 3-CH₃-5-CN Cl N(CH₃)₂ CH₂

TABLE 13 Some of compounds of formula I-2 I-2

(Q₁, Q₂, X₂, X₃, X₄, X₅ = H, Z = O) No. R₁ R₂ (CHR₃)m (R₄)n X₁ Y—R₅ (CHR₆)p 206 CH₃ Cl CH₂ H H NHCH₃ CH₂ 207 CH₃ CH₃ CH₂ H H NHCH₃ CH₂ 208 CH₃ Et CH₂ H H NHCH₃ CH₂ 209 CH₃ n-Pr CH₂ H H NHCH₃ CH₂ 210 CH₃ i-Pr CH₂ H H NHCH₃ CH₂ 211 CH₃ n-Bu CH₂ H H NHCH₃ CH₂ 212 CH₃ i-Bu CH₂ H H NHCH₃ CH₂ 213 CH₃

CH₂ H Cl NHCH₃ CH₂ 214 CH₃ t-Bu CH₂ H H NHCH₃ CH₂ 215 CH₃ CF₃ CH₂ H H NHCH₃ CH₂ 216 CH₃ OCH₃ CH₂ H H NHCH₃ CH₂ 217 CH₃ OEt CH₂ H H NHCH₃ CH₂ 218 CH₃ Ph CH₂ H H NHCH₃ CH₂ 219 CH₃ Ph-4-Cl CH₂ H H NHCH₃ CH₂ 220 CH₃ CH₃ CH₂ H Cl NHCH₃ CH₂ 221 CH₃ Et CH₂ H Cl NHCH₃ CH₂ 222 CH₃ n-Pr CH₂ H Cl NHCH₃ CH₂ 223 CH₃ i-Pr CH₂ H Cl NHCH₃ CH₂ 224 CH₃ n-Bu CH₂ H Cl NHCH₃ CH₂ 225 CH₃ i-Bu CH₂ H Cl NHCH₃ CH₂ 226 CH₃ s-Bu CH₂ H Cl NHCH₃ CH₂ 227 CH₃ t-Bu CH₂ H Cl NHCH₃ CH₂ 228 CH₃ CF₃ CH₂ H Cl NHCH₃ CH₂ 229 CH₃ OCH₃ CH₂ H Cl NHCH₃ CH₂ 230 CH₃ Ph-4-Cl CH₂ H Cl NHCH₃ CH₂ 231 CH₃ CH₃ CH₂ H Br NHCH₃ CH₂ 232 CH₃ Et CH₂ H Br NHOCH₃ CH₂ 233 CH₃ n-Pr CH₂ H Br NHNHCH₃ CH₂ 234 CH₃ OCH₂F CH₂ H Br NHCH₃ CH₂ 235 CH₃ OCH₂CF₃ CH₂ H Cl NHCH₃ CH₂ 236 CH₃ Ph-4-Cl CH₂ H Br NHCH₃ CH₂ 237 CH₃ CF₃ CH₂ H NO₂ NHCH₃ CH₂ 238 CH₃ Et CH₂ H NO₂ NHCH₃ CH₂ 239 CH₃ n-Pr CH₂ H NO₂ NHCH₃ CH₂ 240 CH₃ i-Pr CH₂ H NO₂ NHCH₃ CH₂ 241 CH₃ n-Bu CH₂ H NO₂ NHCH₃ CH₂ 242 CH₃ CF₃ CH₂ H NO₂ NHCH₃ CH₂ 243 CH₃ OCF₃ CH₂ H NO₂ NHCH₃ CH₂ 244 CH₃ Ph-4-Cl CH₂ H NO₂ NHCH₃ CH₂ 245 CH₃ CH₃ CH(CH₃) H CH₃ NHCH₃ CH₂ 246 CH₃ Et CH₂ H Cl NHCH₃ R-*CH(CH₃) 247 CH₃ CF₃ CH₂ H CH₃ NHCH₃ CH₂ 248 CH₃ Ph CH₂ H CH₃ NHCH₃ CH₂ 249 CH₃ Ph-4-Cl CH₂ H CH₃ NHCH₃ CH₂ 250 CH₃ CH₃ CH₂ H CN NHCH₃ CH₂ 251 CH₃ Et CH₂ H Cl NHCH₃ S-*CH(CH₃) 252 CH₃ CF₃ CH₂ H CN NHCH₃ CH₂ 253 CH₃ OCH₃ CH₂ H CN NHCH₃ CH₂ 254 CH₃ Ph-4-Cl CH₂ H CN NHCH₃ CH₂ 255 CH₃ CH₃ CH₂ H SO₂CF₃ NHCH₃ CH₂ 256 CH₃ Et CH₂ H SO₂CF₃ NHCH₃ CH₂ 257 CH₃ CF₃ CH₂ H SO₂CF₃ NHCH₃ CH₂ 258 CH₃ Ph-4-Cl CH₂ H SO₂CF₃ NHCH₃ CH₂ 259 CH₃ CH₃ CH₂ H SOCF₃ NHCH₃ CH₂ 260 CH₃ Et CH₂ H SOCF₃ NHCH₃ CH₂ 261 CH₃ CF₃ CH₂ H SOCF₃ NHCH₃ CH₂ 262 CH₃ Ph-4-Cl CH₂ H SOCF₃ NHCH₃ CH₂ 263 CH₃ CH₃ CH₂ H OCH₃ NHCH₃ CH₂ 264 CH₃ CF₃ CH₂ H OCH₃ NHCH₃ CH₂ 265 CH₃ 4-Cl—Ph CH₂ H OCH₃ NHCH₃ CH₂ 266 CH₃ CH₃ CH(CH₃) H H NHCH₃ CH₂ 267 CH₃ Et CH(CH₃) H Cl NHCH₃ (CH₂)₂ 268 CH₃ OCH₃ CH(CH₃) H H NHCH₃ CH₂ 269 CH₃ Ph-4-Cl CH(CH₃) H H NHCH₃ CH₂ 270 CH₃ CH₃ CH(CH₃) H Cl NHCH₃ CH₂ 271 CH₃ Et R-*CH(CH₃) H Cl NHCH₃ CH₂ 272 CH₃ n-Pr CH(CH₃) H Cl NHCH₃ CH₂ 273 CH₃ i-Pr CH(CH₃) H Cl NHCH₃ CH₂ 274 CH₃ Et S-*CH(CH₃) H Cl NHCH₃ CH₂ 275 CH₃ CF₃ CH(CH₃) H Cl NHCH₃ CH₂ 276 CH₃ Ph-4-Cl CH(CH₃) H Cl NHCH₃ CH₂ 277 CH₃ CH₃ CH(CH₃) H Br NHCH₃ CH₂ 278 CH₃ Et CH(CH₃) H Br NHCH₃ CH₂ 279 CH₃ CH₃ CH(CH₃) H NO₂ NHCH₃ CH₂ 280 CH₃ Et CH(CH₃) H NO₂ NHCH₃ CH₂ 281 CH₃ CF₃ CH(CH₃) H NO₂ NHCH₃ CH₂ 282 CH₃ CH₃ CH₂ H CH₃ NHCH₃ CH₂ 283 CH₃ CH₃ CH(CH₃) H Cl NHCH₃ (CH₂)₂ 284 CH₃ CF₃ CH(CH₃) H CH₃ NHCH₃ CH₂ 285 CH₃ CH₃ (CH₂)₂ H H NHCH₃ CH₂ 286 CH₃ CH₃ (CH₂)₂ H Cl NHCH₃ CH₂ 287 CH₃ Et (CH₂)₂ H H NHCH₃ CH₂ 288 CH₃ Et (CH₂)₂ H Cl NHCH₃ CH₂ 289 CH₃ CH₃ (CH₂)₃ H H NHCH₃ CH₂ 290 CH₃ CH₃ (CH₂)₃ H Cl NHCH₃ CH₂ 291 CH₃ Et (CH₂)₃ H H NHCH₃ CH₂ 292 CH₃ Et (CH₂)₃ H Cl NHCH₃ CH₂ 293 CH₃ CH₃ CH₂ H H OCH₃ CH₂ 294 CH₃ Et CH₂ H H OCH₃ CH₂ 295 CH₃ n-Pr CH₂ H H OCH₃ CH₂ 296 CH₃ i-Pr CH₂ H H OCH₃ CH₂ 297 CH₃ i-Bu CH₂ H H OCH₃ CH₂ 298 H CF₃ CH₂ H H OCH₃ CH₂ 299 CH₃ CH₃ CH₂ 3-CH₃ Cl OEt CH₂ 300 CH₃ CH₃ CH₂ H Cl OEt CH₂ 301 CH₃ n-Pr CH₂ H Cl OCH₃ CH₂ 302 CH₃ i-Pr CH₂ H Cl OCH₃ CH₂ 303 CH₃ i-Bu CH₂ H Cl OCH₃ CH₂ 304 CH₃ Et CH₂ H Cl OEt CH₂ 305 CH₃ t-Bu CH₂ H Cl OCH₃ CH₂ 306 CH₃ CF₃ CH₂ H Cl OCH₃ CH₂ 307 CH₃ OCH₃ CH₂ H Cl OCH₃ CH₂ 308 CH₃ Ph CH₂ H Cl OCH₃ CH₂ 309 Et CH₃ CH₂ H H NHCH₃ CH₂ 310 Et Et CH₂ H H NHCH₃ CH₂ 311 Et CF₃ CH₂ H H OCH₃ CH₂ 312 Et CH₃ CH₂ H Cl NHCH₃ CH₂ 313 Et Et CH₂ H Cl NHCH₃ CH₂ 314 Et n-Pr CH₂ H Cl OCH₃ CH₂ 315 Et i-Pr CH₂ H Cl OCH₃ CH₂ 316 Et CF₃ CH₂ H Cl NHOCH₃ CH₂ 317 2-Py-3-Cl CH₃ CH₂ H H NHCH₃ CH₂ 318 2-Py-3-Cl CF₃ CH₂ H H NHCH₃ CH₂ 319 2-Py-3-Cl Cl CH₂ H H NHCH₃ CH₂ 320 2-Py-3-Cl OCH₂CF₃ CH₂ H H NHCH₃ CH₂ 321 2-Py-3-Cl OCH₂CN CH₂ H H NHCH₃ CH₂ 322 2-Py-3-Cl Br CH₂ H H NHCH₃ CH₂ 323 2-Py-3-Cl Br CH₂ 3-CH₃-5-CN H NHCH₃ CH₂ 324 2-Py-3-Cl OCH₂F CH₂ H H NHCH₃ CH₂ 325 2-Py-3,5-2Cl CF₃ CH₂ H H NHCH₃ CH₂ 326 2-Py-3-Cl Br CH₂ 3-CH₃-5-Br H NHCH₃ CH₂ 327 2-Py-3,5-2Cl CH₃ CH₂ H H NHCH₃ CH₂ 328 2-Py-3,5-2Cl Br CH₂ H H NHCH₃ CH₂ 329 2-Py-3-Cl-5-CF₃ Br CH₂ H H NHCH₃ CH₂ 330 2-Py-3-Cl-5-CF₃ CH₃ CH₂ H H NHCH₃ CH₂ 331 2-Py-3-Cl-5-CF₃ CH₃ CH₂ H H NHCH₃ CH₂ 332 2-Py-5-CF₃ CH₃ CH₂ H H NHCH₃ CH₂ 333 2-Py-5-CF₃ Cl CH₂ H H NHCH₃ CH₂ 334 H CF₃ CH₂ H H NHCH₃ CH₂ 335 H CH₃ CH₂ H Cl NHCH₃ CH₂ 336 H Et CH₂ H Cl NHCH₃ CH₂ 337 H CF₃ CH₂ H Cl NHCH₃ CH₂ 338 CH₃ CH₃ CH₂ H H NHEt CH₂ 339 CH₃ Et CH₂ H H NHEt CH₂ 340 CH₃ OCH₂CF₃ CH₂ H H NHCH₃ CH₂ 341 CH₃ CH₂OCH₃ CH₂ H H NHCH₃ CH₂ 342 CH₃ CF₃ CH₂ H H NHEt CH₂ 343 CH₃ CH₃ CH₂ H Cl NHEt CH₂ 344 CH₃ Et CH₂ H Cl NHEt CH₂ 345 CH₃ OCH₂CN CH₂ H Cl NHCH₃ CH₂ 346 CH₃ Et CH₂ 5-F Cl NHEt CH₂ 347 CH₃ CF₃ CH₂ H Cl NHEt CH₂ 348 CH₃ CH₃ CH₂ H H N(CH₃)₂ CH₂ 349 CH₃ Et CH₂ H H N(CH₃)₂ CH₂ 350 CH₃ n-Pr CH₂ H H N(CH₃)₂ CH₂ 351 CH₃ CF₃ CH₂ H H N(CH₃)₂ CH₂ 352 CH₃ CH₃ CH₂ H Cl N(CH₃)₂ CH₂ 353 CH₃ Et CH₂ H Cl N(CH₃)₂ CH₂ 354 CH₃ i-Pr CH₂ H Cl N(CH₃)₂ CH₂ 355 CH₃ CF₃ CH₂ H Cl N(CH₃)₂ CH₂ 356 CH₃ CH₃ CH₂ H H NH₂ CH₂ 357 CH₃ Et CH₂ H H NH₂ CH₂ 358 CH₃ n-Pr CH₂ 3-CH₃-4-CN H NH₂ CH₂ 359 CH₃ 3-Py CH₂ H H NH₂ CH₂ 360 CH₃ CF₃ CH₂ H H NII₂ CH₂ 361 CH₃ CH₃ CH₂ H Cl NH₂ CH₂ 362 CH₃ Et CH₂ H Cl NH₂ CH₂ 363 CH₃ n-Pr CH₂ 2-CH₃-5-I Cl NH₂ CH₂ 364 CH₃ i-Pr CH₂ H Cl NH₂ CH₂ 365 CH₃ CF₃ CH₂ H Cl NH₂ CH₂ 366 CH₃ CH₃ CH₂ 5-Cl H NHCH₃ CH₂ 367 CH₃ CH₃ CH₂ 3-CH₃-5-I Cl NHCH₃ CH₂ 368 CH₃ CH₃ CH₂ 3-CH₃-5-Cl H NHCH₃ CH₂ 369 CH₃ CH₃ CH₂ 3-CH₃ H NHCH₃ CH₂ 370 CH₃ CH₃ CH₂ 5-Br H NHCH₃ CH₂ 371 CH₃ CH₃ CH₂ 3-CH₃-5-Br Cl NHCH₃ CH₂ 372 CH₃ CH₃ CH₂ 3-CH₃-5-CN Cl NHCH₃ CH₂ 373 CH₃ CH₃ CH₂ 3,5-2Cl H NHCH₃ CH₂ 374 CH₃ CH₃ CH₂ 5-F H NHCH₃ CH₂ 375 CH₃ Et CH₂ 3-CH₃ Cl NHCH₃ CH₂ 376 CH₃ CH₃ CH₂ 3-CH₃ Cl NHCH₃ CH₂ 377 CH₃ Et CH₂ 3-CH₃-5-Cl Cl NHCH₃ CH₂ 378 Ph CH₃ CH₂ H Cl NHCH₃ CH₂ 379 Ph-4-Cl CH₃ CH₂ H Cl NHCH₃ CH₂ 380 Ph CH₃ CH₂ H H NHCH₃ (CH₂)₃ 381 Ph-4-Cl CH₃ CH₂ H H NHCH₃ (CH₂)₃ 382 CH₃ CH₃ CH₂ 3-CH₃ H NHEt CH₂ 383 CH₃ Et CH₂ 3-CH₃ Cl OEt CH₂ 384 CH₃ CH₃ CH₂ 5-F H NHCH₃ CH₂ 385 CH₃ CH₃ CH₂ 3-CH₃-5-CN Cl NHCH₃ CH₂ 386 CH₃ Et CH₂ 3-CH₃-5-Br Cl NHCH₃ CH₂ 387 CH₃ CH₃ CH₂ 3-CH₃-5-Cl Cl NHCH₃ CH₂ 388 CH₃ Et CH₂ 3,5-2Cl Cl NHCH₃ CH₂ 389 CH₃ CH₃ CH₂ 5-CH₃-3-Cl H NHEt CH₂ 390 CH₃ Et CH₂ 3-CN-5-CH₃ Cl OEt CH₂ 391 CH₃ CH₃ CH₂ H Cl NHCH₃ (CH₂)₂ 392 CH₃ Et CH₂ H Cl NHCH₃ (CH₂)₂ 393 CH₃ CH₃ CH₂ 5-F H NHCH₃ CH₂ 394 2-Py-3-Cl Br CH₂ 3-CH₃-5-Cl H NHCH₃ CH₂ 395 CH₃ CH₃ CH₂ 3-CH₃-5-CN H NHCH₃ CH₂ 396 2-Py-3-Cl Br CH₂ 3,5-2Cl H NHCH₃ CH₂ 397 2-Py-3-Cl CH₃ CH₂ 3-CH₃ H NHCH₃ CH₂ 398 CH₃ Et CH₂ 3-CH₃-5-CN Cl NHCH₃ CH₂ 399 CH₃ CH₃ CH₂ H Cl NHCH₃ (CH₂)₃ 400 CH₃ Et CH₂ H Cl

CH₂ 401 CH₃ CH₃ CH₂ H H

CH₂ 402 CH₃ Et CH₂ H H

CH₂ 403 CH₃ CH₃ CH₂ H Cl

CH₂ 404 CH₃ CH₃ CH₂ H CH₃ NHCH₃ (CH₂)₃ 405 CH₃ CH₃ CH₂ H Cl N(CH₃)₂ — 406 CH₃ Et CH₂ H Cl N(CH₃)₂ — 407 CH₃ CH₃ CH₂ H Cl NHCH₃ — 408 CH₃ Et CH₂ H Cl N(CH₃)₂ — 409 CH₃ CH₃ CH₂ 3-CH₃-5-Cl Cl N(CH₃)₂ CH₂ 410 CH₃ Et CH₂ 3-CH₃-5-CN Cl N(CH₃)₂ CH₂

TABLE 14 Some of compounds of formula I-3 I-3

(Q₁, Q₂, X₂, X₃, X₄, X₅ = H, Z = O) No. R₁ R₂ (CHR₃)m (R₄)n X₁ Y—R₅ (CHR₆)p 411 CH₃ Cl CH₂ H H NHCH₃ CH₂ 412 CH₃ CH₃ CH₂ H H NHCH₃ CH₂ 413 CH₃ Et CH₂ H H NHCH₃ CH₂ 414 CH₃ n-Pr CH₂ H H NHCH₃ CH₂ 415 CH₃ i-Pr CH₂ H H NHCH₃ CH₂ 416 CH₃ n-Bu CH₂ H H NHCH₃ CH₂ 417 CH₃ i-Bu CH₂ H H NHCH₃ CH₂ 418 CH₃

CH₂ H Cl NHCH₃ CH₂ 419 CH₃ t-Bu CH₂ H H NHCH₃ CH₂ 420 CH₃ CF₃ CH₂ H H NHCH₃ CH₂ 421 CH₃ OCH₃ CH₂ H H NHCH₃ CH₂ 422 CH₃ OEt CH₂ H H NHCH₃ CH₂ 423 CH₃ Ph CH₂ H H NHCH₃ CH₂ 424 CH₃ Ph-4-Cl CH₂ H H NHCH₃ CH₂ 425 CH₃ CH₃ CH₂ H Cl NHCH₃ CH₂ 426 CH₃ Et CH₂ H Cl NHCH₃ CH₂ 427 CH₃ n-Pr CH₂ H Cl NHCH₃ CH₂ 428 CH₃ i-Pr CH₂ H Cl NHCH₃ CH₂ 429 CH₃ n-Bu CH₂ H Cl NHCH₃ CH₂ 430 CH₃ i-Bu CH₂ H Cl NHCH₃ CH₂ 431 CH₃ s-Bu CH₂ H Cl NHCH₃ CH₂ 432 CH₃ t-Bu CH₂ H Cl NHCH₃ CH₂ 433 CH₃ CF₃ CH₂ H Cl NHCH₃ CH₂ 434 CH₃ OCH₃ CH₂ H Cl NHCH₃ CH₂ 435 CH₃ Ph-4-Cl CH₂ H Cl NHCH₃ CH₂ 436 CH₃ CH₃ CH₂ H Br NHCH₃ CH₂ 437 CH₃ Et CH₂ H Br NHOCH₃ CH₂ 438 CH₃ n-Pr CH₂ H Br NHNHCH₃ CH₂ 439 CH₃ OCH₂F CH₂ H Br NHCH₃ CH₂ 440 CH₃ OCH₂CF₃ CH₂ H Cl NHCH₃ CH₂ 441 CH₃ Ph-4-Cl CH₂ H Br NHCH₃ CH₂ 442 CH₃ CF₃ CH₂ H NO₂ NHCH₃ CH₂ 443 CH₃ Et CH₂ H NO₂ NHCH₃ CH₂ 444 CH₃ n-Pr CH₂ H NO₂ NHCH₃ CH₂ 445 CH₃ i-Pr CH₂ H NO₂ NHCH₃ CH₂ 446 CH₃ n-Bu CH₂ H NO₂ NHCH₃ CH₂ 447 CH₃ CF₃ CH₂ H NO₂ NHCH₃ CH₂ 448 CH₃ OCF₃ CH₂ H NO₂ NHCH₃ CH₂ 449 CH₃ Ph-4-Cl CH₂ H NO₂ NHCH₃ CH₂ 450 CH₃ CH₃ CH(CH₃) H CH₃ NHCH₃ CH₂ 451 CH₃ Et CH₂ H Cl NHCH₃ R-*CH(CH₃) 452 CH₃ CF₃ CH₂ H CH₃ NHCH₃ CH₂ 453 CH₃ Ph CH₂ H CH₃ NHCH₃ CH₂ 454 CH₃ Ph-4-Cl CH₂ H CH₃ NHCH₃ CH₂ 455 CH₃ CH₃ CH₂ H CN NHCH₃ CH₂ 456 CH₃ Et CH₂ H Cl NHCH₃ S-*CH(CH₃) 457 CH₃ CF₃ CH₂ H CN NHCH₃ CH₂ 458 CH₃ OCH₃ CH₂ H CN NHCH₃ CH₂ 459 CH₃ Ph-4-Cl CH₂ H CN NHCH₃ CH₂ 460 CH₃ CH₃ CH₂ H SO₂CF₃ NHCH₃ CH₂ 461 CH₃ Et CH₂ H SO₂CF₃ NHCH₃ CH₂ 462 CH₃ CF₃ CH₂ H SO₂CF₃ NHCH₃ CH₂ 463 CH₃ Ph-4-Cl CH₂ H SO₂CF₃ NHCH₃ CH₂ 464 CH₃ CH₃ CH₂ H SOCF₃ NHCH₃ CH₂ 465 CH₃ Et CH₂ H SOCF₃ NHCH₃ CH₂ 466 CH₃ CF₃ CH₂ H SOCF₃ NHCH₃ CH₂ 467 CH₃ Ph-4-Cl CH₂ H SOCF₃ NHCH₃ CH₂ 469 CH₃ CH₃ CH₂ H OCH₃ NHCH₃ CH₂ 469 CH₃ CF₃ CH₂ H OCH₃ NHCH₃ CH₂ 470 CH₃ Ph-4-Cl CH₂ H OCH₃ NHCH₃ CH₂ 471 CH₃ CH₃ CH(CH₃) H H NHCH₃ CH₂ 472 CH₃ Et CH(CH₃) H Cl NHCH₃ (CH₂)₂ 473 CH₃ OCH₃ CH(CH₃) H H NHCH₃ CH₂ 474 CH₃ Ph-4-Cl CH(CH₃) H H NHCH₃ CH₂ 475 CH₃ CH₃ CH(CH₃) H Cl NHCH₃ CH₂ 476 CH₃ Et R-*CH(CH₃) H Cl NHCH₃ CH₂ 477 CH₃ n-Pr CH(CH₃) H Cl NHCH₃ CH₂ 478 CH₃ i-Pr CH(CH₃) H Cl NHCH₃ CH₂ 479 CH₃ Et S-*CH(CH₃) H Cl NHCH₃ CH₂ 480 CH₃ CF₃ CH(CH₃) H Cl NHCH₃ CH₂ 481 CH₃ Ph-4-Cl CH(CH₃) H Cl NHCH₃ CH₂ 482 CH₃ CH₃ CH(CH₃) H Br NHCH₃ CH₂ 483 CH₃ Et CH(CH₃) H Br NHCH₃ CH₂ 484 CH₃ CH₃ CH(CH₃) H NO₂ NHCH₃ CH₂ 485 CH₃ Et CH(CH₃) H NO₂ NHCH₃ CH₂ 486 CH₃ CF₃ CH(CH₃) H NO₂ NHCH₃ CH₂ 487 CH₃ CH₃ CH₂ H CH₃ NHCH₃ CH₂ 488 CH₃ CH₃ CH(CH₃) H Cl NHCH₃ (CH₂)₂ 489 CH₃ CF₃ CH(CH₃) H CH₃ NHCH₃ CH₂ 490 CH₃ CH₃ (CH₂)₂ H H NHCH₃ CH₂ 491 CH₃ CH₃ (CH₂)₂ H Cl NHCH₃ CH₂ 492 CH₃ Et (CH₂)₂ H H NHCH₃ CH₂ 493 CH₃ Et (CH₂)₂ H Cl NHCH₃ CH₂ 494 CH₃ CH₃ (CH₂)₃ H H NHCH₃ CH₂ 495 CH₃ CH₃ (CH₂)₃ H Cl NHCH₃ CH₂ 496 CH₃ Et (CH₂)₃ H H NHCH₃ CH₂ 497 CH₃ Et (CH₂)₃ H Cl NHCH₃ CH₂ 498 CH₃ CH₃ CH₂ H H OCH₃ CH₂ 499 CH₃ Et CH₂ H H OCH₃ CH₂ 500 CH₃ n-Pr CH₂ H H OCH₃ CH₂ 501 CH₃ i-Pr CH₂ H H OCH₃ CH₂ 502 CH₃ i-Bu CH₂ H H OCH₃ CH₂ 503 H CF₃ CH₂ H H OCH₃ CH₂ 504 CH₃ CH₃ CH₂ 3-CH₃ Cl OEt CH₂ 505 CH₃ CH₃ CH₂ H Cl OEt CH₂ 506 CH₃ n-Pr CH₂ H Cl OCH₃ CH₂ 507 CH₃ i-Pr CH₂ H Cl OCH₃ CH₂ 508 CH₃ i-Bu CH₂ H Cl OCH₃ CH₂ 509 CH₃ Et CH₂ H Cl OEt CH₂ 510 CH₃ t-Bu CH₂ H Cl OCH₃ CH₂ 511 CH₃ CF₃ CH₂ H Cl OCH₃ CH₂ 512 CH₃ OCH₃ CH₂ H Cl OCH₃ CH₂ 513 CH₃ Ph CH₂ H Cl OCH₃ CH₂ 514 Et CH₃ CH₂ H H NHCH₃ CH₂ 515 Et Et CH₂ H H NHCH₃ CH₂ 516 Et CF₃ CH₂ H H OCH₃ CH₂ 517 Et CH₃ CH₂ H Cl NHCH₃ CH₂ 518 Et Et CH₂ H Cl NHCH₃ CH₂ 519 Et n-Pr CH₂ H Cl OCH₃ CH₂ 520 Et i-Pr CH₂ H Cl OCH₃ CH₂ 521 Et CF₃ CH₂ H Cl NHOCH₃ CH₂ 522 2-Py-3-Cl CH₃ CH₂ H H NHCH₃ CH₂ 523 2-Py-3-Cl CF₃ CH₂ H H NHCH₃ CH₂ 524 2-Py-3-Cl Cl CH₂ H H NHCH₃ CH₂ 525 2-Py-3-Cl OCH₂CF₃ CH₂ H H NHCH₃ CH₂ 526 2-Py-3-Cl OCH₂CN CH₂ H H NHCH₃ CH₂ 527 2-Py-3-Cl Br CH₂ H H NHCH₃ CH₂ 528 2-Py-3-Cl Br CH₂ 3-CH₃-5-CN H NHCH₃ CH₂ 529 2-Py-3-Cl OCH₂F CH₂ H H NHCH₃ CH₂ 530 2-Py-3,5-2Cl CF₃ CH₂ H H NHCH₃ CH₂ 531 2-Py-3-Cl Br CH₂ 3-CH₃-5-Br H NHCH₃ CH₂ 532 2-Py-3,5-2Cl CH₃ CH₂ H H NHCH₃ CH₂ 533 2-Py-3,5-2Cl Br CH₂ H H NHCH₃ CH₂ 534 2-Py-3-Cl-5-CF₃ Br CH₂ H H NHCH₃ CH₂ 535 2-Py-3-Cl-5-CF₃ CH₃ CH₂ H H NHCH₃ CH₂ 536 2-Py-3-Cl-5-CF₃ CH₃ CH₂ H H NHCH₃ CH₂ 537 2-Py-5-CF₃ CH₃ CH₂ H H NHCH₃ CH₂ 538 2-Py-5-CF₃ Cl CH₂ H H NHCH₃ CH₂ 539 H CF₃ CH₂ H H NHCH₃ CH₂ 540 H CH₃ CH₂ H Cl NHCH₃ CH₂ 541 H Et CH₂ H Cl NHCH₃ CH₂ 542 H CF₃ CH₂ H Cl NHCH₃ CH₂ 543 CH₃ CH₃ CH₂ H H NHEt CH₂ 544 CH₃ Et CH₂ H H NHEt CH₂ 545 CH₃ OCH₂CF₃ CH₂ H H NHCH₃ CH₂ 546 CH₃ CH₂OCH₃ CH₂ H H NHCH₃ CH₂ 547 CH₃ CF₃ CH₂ H H NHEt CH₂ 548 CH₃ CH₃ CH₂ H Cl NHEt CH₂ 549 CH₃ Et CH₂ H Cl NHEt CH₂ 550 CH₃ OCH₂CN CH₂ H Cl NHCH₃ CH₂ 551 CH₃ Et CH₂ 5-F Cl NHEt CH₂ 552 CH₃ CF₃ CH₂ H Cl NHEt CH₂ 553 CH₃ CH₃ CH₂ H H N(CH₃)₂ CH₂ 554 CH₃ Et CH₂ H H N(CH₃)₂ CH₂ 555 CH₃ n-Pr CH₂ H H N(CH₃)₂ CH₂ 556 CH₃ CF₃ CH₂ H H N(CH₃)₂ CH₂ 557 CH₃ CH₃ CH₂ H Cl N(CH₃)₂ CH₂ 558 CH₃ Et CH₂ H Cl N(CH₃)₂ CH₂ 559 CH₃ i-Pr CH₂ H Cl N(CH₃)₂ CH₂ 560 CH₃ CF₃ CH₂ H Cl N(CH₃)₂ CH₂ 561 CH₃ CH₃ CH₂ H H NH₂ CH₂ 562 CH₃ Et CH₂ H H NH₂ CH₂ 563 CH₃ n-Pr CH₂ 3-CH₃-4-CN H NH₂ CH₂ 564 CH₃ 3-Py CH₂ H H NH₂ CH₂ 565 CH₃ CF₃ CH₂ H H NII₂ CH₂ 566 CH₃ CH₃ CH₂ H Cl NH₂ CH₂ 567 CH₃ Et CH₂ H Cl NH₂ CH₂ 568 CH₃ n-Pr CH₂ 2-CH₃-5-I Cl NH₂ CH₂ 569 CH₃ i-Pr CH₂ H Cl NH₂ CH₂ 570 CH₃ CF₃ CH₂ H Cl NH₂ CH₂ 571 CH₃ CH₃ CH₂ 5-Cl H NHCH₃ CH₂ 572 CH₃ CH₃ CH₂ 3-CH₃-5-I Cl NHCH₃ CH₂ 573 CH₃ CH₃ CH₂ 3-CH₃-5-Cl H NHCH₃ CH₂ 574 CH₃ CH₃ CH₂ 3-CH₃ H NHCH₃ CH₂ 575 CH₃ CH₃ CH₂ 5-Br H NHCH₃ CH₂ 576 CH₃ CH₃ CH₂ 3-CH₃-5-Br Cl NHCH₃ CH₂ 577 CH₃ CH₃ CH₂ 3-CH₃-5-CN Cl NHCH₃ CH₂ 578 CH₃ CH₃ CH₂ 3,5-2Cl H NHCH₃ CH₂ 579 CH₃ CH₃ CH₂ 5-F H NHCH₃ CH₂ 580 CH₃ Et CH₂ 3-CH₃ Cl NHCH₃ CH₂ 581 CH₃ CH₃ CH₂ 3-CH₃ Cl NHCH₃ CH₂ 582 CH₃ Et CH₂ 3-CH₃-5-Cl Cl NHCH₃ CH₂ 583 Ph CH₃ CH₂ H Cl NHCH₃ CH₂ 584 Ph-4-Cl CH₃ CH₂ H Cl NHCH₃ CH₂ 585 Ph CH₃ CH₂ H H NHCH₃ (CH₂)₃ 586 Ph-4-Cl CH₃ CH₂ H H NHCH₃ (CH₂)₃ 587 CH₃ CH₃ CH₂ 3-CH₃ H NHEt CH₂ 588 CH₃ Et CH₂ 3-CH₃ Cl OEt CH₂ 589 CH₃ CH₃ CH₂ 5-F H NHCH₃ CH₂ 590 CH₃ CH₃ CH₂ 3-CH₃-5-CN Cl NHCH₃ CH₂ 591 CH₃ Et CH₂ 3-CH₃-5-Br Cl NHCH₃ CH₂ 592 CH₃ CH₃ CH₂ 3-CH₃-5-Cl Cl NHCH₃ CH₂ 593 CH₃ Et CH₂ 3,5-2Cl Cl NHCH₃ CH₂ 594 CH₃ CH₃ CH₂ 5-CH₃-3-Cl H NHEt CH₂ 595 CH₃ Et CH₂ 3-CN-5-CH₃ Cl OEt CH₂ 596 CH₃ CH₃ CH₂ H Cl NHCH₃ (CH₂)₂ 597 CH₃ Et CH₂ H Cl NHCH₃ (CH₂)₂ 598 CH₃ CH₃ CH₂ 5-F H NHCH₃ CH₂ 599 2-Py-3-Cl Br CH₂ 3-CH₃-5-Cl H NHCH₃ CH₂ 600 CH₃ CH₃ CH₂ 3-CH₃-5-CN H NHCH₃ CH₂ 601 2-Py-3-C Br CH₂ 3,5-2Cl H NHCH₃ CH₂ 602 2-Py-3-C CH₃ CH₂ 3-CH₃ H NHCH₃ CH₂ 603 CH₃ Et CH₂ 3-CH₃-5-CN Cl NHCH₃ CH₂ 604 CH₃ CH₃ CH₂ H Cl NHCH₃ (CH₂)₃ 605 CH₃ Et CH₂ H Cl

CH₂ 606 CH₃ CH₃ CH₂ H H

CH₂ 607 CH₃ Et CH₂ H H

CH₂ 608 CH₃ CH₃ CH₂ H Cl

CH₂ 609 CH₃ CH₃ CH₂ H CH₃ NHCH₃ (CH₂)₃ 610 CH₃ CH₃ CH₂ H Cl N(CH₃)₂ — 611 CH₃ Et CH₂ H Cl N(CH₃)₂ — 612 CH₃ CH₃ CH₂ H Cl NHCH₃ — 613 CH₃ Et CH₂ H Cl N(CH₃)₂ — 614 CH₃ CH₃ CH₂ 3-CH₃-5-Cl Cl N(CH₃)₂ CH₂ 615 CH₃ Et CH₂ 3-CH₃-5-CN Cl N(CH₃)₂ CH₂

The abbreviations in the tables above of Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, Bn, Py and Ph respectively represents ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, benzyl, pyridyl and phenyl. In tables 12, 13 and 14, “—” represents p0, namely chemical bond, namely means the two chemical groups are connected directly.

The other compounds of the present invention are listed in table 15, wherein: R₃═R₆=Q₁=Q₂=X₂═X₄═H, p=1, m=1, n=0, Z=0, YR₅═NHCH₃, N-Q₂ links with phenyl ring at the 2-position.

TABLE 15

compound R₁ R₂ X₁ X₃ X₅ 616 CH₃ CH₃ Cl H Cl 617 CH₃ Et Cl H Cl 618 CH₃ n-Pr Cl H Cl 619 CH₃ i-Pr Cl H Cl 620 CH₃ t-Bu Cl H Cl 621 CH₃

Cl H Cl 622 CH₃ CF₃ Cl H Cl 623 CH₃ CH₂OCH₃ Cl H Cl 624 CH₃ CH₂OCH₂CF₃ Cl H Cl 625 CH₃ CH₂Cl Cl H Cl 626 CH₃ CH₂CN Cl H Cl 627 CH₃ Cl Cl H Cl 628 CH₃ Br Cl H Cl 629 CH₃ OCF3 Cl H Cl 630 CH₃ OCH₂CF3 Cl H Cl 631 CH₃ OCH₂CN Cl H Cl 632 CH₃ Ph Cl H Cl 633 CH₃ Ph-4-Cl Cl H Cl 634 CH₃ Ph-2,4-2Cl Cl H Cl 635 CH₃ Ph-4-CH₃ Cl H Cl 636 CH₃ Ph-2,4-2CH₃ Cl H Cl 637 CH₃ Ph-4-CF₃ Cl H Cl 638 CH₃ Ph-4-OCF₃ Cl H Cl 639 CH₃ 3-Py-2-Cl Cl H Cl 640 CH₃ 2-Py-5-Cl Cl H Cl 641 CH₃ 3-Py Cl H Cl 642 CH₃ CH₃ H H Cl 643 CH₃ Et H H Cl 644 CH₃ n-Pr H H Cl 645 CH₃ i-Pr H H Cl 646 CH₃ t-Bu H H Cl 647 CH₃

H H Cl 648 CH₃ CF₃ H H Cl 649 CH₃ CH₃ Br H Cl 650 CH₃ Et Br H Cl 651 CH₃ n-Pr Br H Cl 652 CH₃ i-Pr Br H Cl 653 CH₃ t-Bu Br H Cl 654 CH₃

Br H Cl 655 CH₃ CF₃ Br H Cl 656 Et CH₃ H H Cl 657 Et Et H H Cl 658 Et n-Pr H H Cl 659 Et i-Pr H H Cl 660 Et t-Bu H H Cl 661 Et

H H Cl 662 Et CF₃ H H Cl 663 Et CH₃ Cl H Cl 664 Et Et Cl H Cl 665 Et n-Pr Cl H Cl 666 Et i-Pr Cl H Cl 667 Et t-Bu Cl H Cl 668 Et

Cl H Cl 669 Et CF₃ Cl H Cl 670 i-Pr CH₃ Cl H Cl 671 i-Pr CH₃ H H Cl 672

CH₃ Cl H Cl 673

CH₃ H H Cl 674 CH₂CF₃ CH₃ Cl H Cl 675 CH₂CF₃ CH₃ H H Cl 676 Ph CH₃ Cl H Cl 677 Ph CH₃ H H Cl 678 Ph Cl H H Cl 679 Ph Br H H Cl 680 Ph-2-Cl CH₃ Cl H Cl 681 Ph-2-Cl CH₃ H H Cl 682 Ph-2-Cl Cl H H Cl 683 Ph-2-Cl Br H H Cl 684 Ph-4-Cl CH₃ Cl H Cl 685 Ph-4-Cl CH₃ H H Cl 686 Ph-4-Cl Cl H H Cl 687 Ph-4-Cl Br H H Cl 688 2-Py-3-Cl CH₃ Cl H Cl 689 2-Py-3-Cl CH₃ H H Cl 690 2-Py-3-Cl Cl H H Cl 691 2-Py-3-Cl Br H H Cl 692 2-Py-3-Cl CF₃ H H Cl 693 2-Py-3-Cl CHF₂ H H Cl 694 2-Py-3-Cl OCF3 H H Cl 695 2-Py-3-Cl OCH₂CF3 H H Cl 696 2-Py-3-Cl OCH₂CN H H Cl 697 2-Py-3-Cl OCH₂F H H Cl 698 2-Py-3,5-2Cl Cl H H Cl 699 2-Py-3,5-2Cl Br H H Cl 670 2-Py-3,5,6-3Cl Cl H H Cl 671 2-Py-3,5,6-3Cl Br H H Cl 672 2-Py-3-Cl-5-CF₃ Cl H H Cl 673 2-Py-3-Cl-5-CF₃ Br H H Cl 674 2-Py-5-CF₃ Cl H H Cl 675 2-Py-5-CF₃ Br H H Cl 676 2-Py-3-Cl-5-CH₃ Cl H H Cl 677 2-Py-3-Cl-5-CH₃ Br H H Cl 678 CH₃ CH₃ Cl H OCH₃ 679 CH₃ Et Cl H OCH₃ 680 CH₃ n-Pr Cl H OCH₃ 681 CH₃ i-Pr Cl H OCH₃ 682 CH₃ t-Bu Cl H OCH₃ 683 CH₃

Cl H OCH₃ 684 CH₃ CF₃ Cl H OCH₃ 685 CH₃ CH₂OCH₃ Cl H OCH₃ 686 CH₃ CH₂OCH₂CF₃ Cl H OCH₃ 687 CH₃ CH₂Cl Cl H OCH₃ 688 CH₃ CH₂CN Cl H OCH₃ 689 CH₃ Cl Cl H OCH₃ 690 CH₃ Br Cl H OCH₃ 691 CH₃ OCF3 Cl H OCH₃ 692 CH₃ OCH₂CF3 Cl H OCH₃ 693 CH₃ OCH₂CN Cl H OCH₃ 694 CH₃ Ph Cl H OCH₃ 695 CH₃ Ph-4-Cl Cl H OCH₃ 696 CH₃ Ph-2,4-2Cl Cl H OCH₃ 697 CH₃ Ph-4-CH₃ Cl H OCH₃ 698 CH₃ Ph-2,4-2CH₃ Cl H OCH₃ 699 CH₃ Ph-4-CF₃ Cl H OCH₃ 700 CH₃ Ph-4-OCF₃ Cl H OCH₃ 701 CH₃ 3-Py-2-Cl Cl H OCH₃ 702 CH₃ 2-Py-5-Cl Cl H OCH₃ 703 CH₃ 3-Py Cl H OCH₃ 704 CH₃ CH₃ H H OCH₃ 705 CH₃ Et H H OCH₃ 706 CH₃ n-Pr H H OCH₃ 707 CH₃ I-Pr H H OCH₃ 708 CH₃ t-Bu H H OCH₃ 709 CH₃

H H OCH₃ 710 CH₃ CF₃ H H OCH₃ 711 CH₃ CH₃ Br H OCH₃ 712 CH₃ Et Br H OCH₃ 713 CH₃ n-Pr Br H OCH₃ 714 CH₃ i-Pr Br H OCH₃ 715 CH₃ t-Bu Br H OCH₃ 716 CH₃

Br H OCH₃ 717 CH₃ CF₃ Br H OCH₃ 718 Et CH₃ H H OCH₃ 719 Et Et H H OCH₃ 720 Et n-Pr H H OCH₃ 721 Et i-Pr H H OCH₃ 722 Et t-Bu H H OCH₃ 723 Et

H H OCH₃ 724 Et CF₃ H H OCH₃ 725 Et CH₃ Cl H OCH₃ 726 Et Et Cl H OCH₃ 727 Et n-Pr Cl H OCH₃ 728 Et i-Pr Cl H OCH₃ 729 Et t-Bu Cl H OCH₃ 730 Et

Cl H OCH₃ 731 Et CF₃ Cl H OCH₃ 732 i-Pr CH₃ Cl H OCH₃ 733 i-Pr CH₃ H H OCH₃ 734

CH₃ Cl H OCH₃ 735

CH₃ H H OCH₃ 736 CH₂CF₃ CH₃ Cl H OCH₃ 737 CH₂CF₃ CH₃ H H OCH₃ 738 Ph CH₃ Cl H OCH₃ 739 Ph CH₃ H H OCH₃ 740 Ph Cl H H OCH₃ 741 Ph Br H H OCH₃ 742 Ph-2-Cl CH₃ Cl H OCH₃ 743 Ph-2-Cl CH₃ H H OCH₃ 744 Ph-2-Cl Cl H H OCH₃ 745 Ph-2-Cl Br H H OCH₃ 746 Ph-4-Cl CH₃ Cl H OCH₃ 747 Ph-4-Cl CH₃ H H OCH₃ 748 Ph-4-Cl Cl H H OCH₃ 749 Ph-4-Cl Br H H OCH₃ 750 2-Py-3-Cl CH₃ Cl H OCH₃ 751 2-Py-3-Cl CH₃ H H OCH₃ 752 2-Py-3-Cl Cl H H OCH₃ 753 2-Py-3-Cl Br H H OCH₃ 754 2-Py-3-Cl CF₃ H H OCH₃ 755 2-Py-3-Cl CHF₂ H H OCH₃ 756 2-Py-3-Cl OCF3 H H OCH₃ 757 2-Py-3-Cl OCH₂CF3 H H OCH₃ 758 2-Py-3-Cl OCH₂CN H H OCH₃ 759 2-Py-3-Cl OCH₂F H H OCH₃ 760 2-Py-3,5-2Cl Cl H H OCH₃ 761 2-Py-3,5-2Cl Br H H OCH₃ 762 2-Py-3,5,6-3Cl Cl H H OCH₃ 763 2-Py-3,5,6-3Cl Br H H OCH₃ 764 2-Py-3-Cl-5-CF₃ Cl H H OCH₃ 765 2-Py-3-Cl-5-CF₃ Br H H OCH₃ 766 2-Py-5-CF₃ Cl H H OCH₃ 767 2-Py-5-CF₃ Br H H OCH₃ 768 2-Py-3-Cl-5-CH₃ Cl H H OCH₃ 769 2-Py-3-Cl-5-CH₃ Br H H OCH₃ 770 CH₃ CH₃ Cl Cl Cl 771 CH₃ Et Cl Cl Cl 772 CH₃ CF₃ Cl Cl Cl 773 CH₃ CH₃ Cl Cl Cl 774 CH₃ Et Cl Cl Cl 775 CH₃ CF₃ Cl Cl Cl 776 CH₃ CH₃ H Cl Cl 777 CH₃ Et H Cl Cl 778 CH₃ CF₃ H Cl Cl 779 CH₃ CH₃ H Cl Cl 780 CH₃ Et H Cl Cl 781 CH₃ CF₃ H Cl Cl 782 CH₃ CH₃ Cl Cl OCH₃ 783 CH₃ Et Cl Cl OCH₃ 784 CH₃ CF₃ Cl Cl OCH₃ 785 CH₃ CH₃ Cl Cl OCH₃ 786 CH₃ Et Cl Cl OCH₃ 787 CH₃ CF₃ Cl Cl OCH₃

Another part of compounds of the present invention are listed in table 16, wherein: R₃═R₆=Q₁=Q₂=X₂═X₄═H, p=2, m=1, n=0, Z═O, YR₅═NHCH₃, N-Q₂ links with phenyl ring at the 2-position.

TABLE 16

The substituents of compounds 788-959 in table 16 in turns correspond to the substituents of compounds 616-787 in table 15.

Another part of compounds of the present invention are listed in table 17, wherein: R₃═CH₃, R₆=Q₁=Q₂=X₂═X₄═H, p=2, m=1, n=0, Z=0, YR₅═NHCH₃, N-Q₂ links with phenyl ring at the 2-position.

TABLE 17

The substituents of compounds 960-1131 in table 17 in turns correspond to the substituents of compounds 616-787 in table 15.

The compounds having general formula (I) exhibit preferably fungicidal activities on plant pathogen such as rice blast, powdery mildew, rust, downy mildew, etc., and in particular, a better prevention and controlling effect on cucumber downy mildew, rice blast and corn rust. The compounds mentioned can be used as active ingredient in agricultural field such as farming and gardening. Therefore, a further object of the present invention relates to the use of the compounds having general formula (I) as fungicides, both in agriculture and other fields. For example, the use of the compounds having general formula (I) used to prepare fungicidal drugs. The plant pathogen prevented by the compounds of the present invention is not limited to the harmful fungus mentioned above.

Due to their positive performance, the compounds mentioned above can be advantageously used in protecting crops of farming and gardening, domestic and breeding animals, as well as environments frequented by human beings, from pathogens.

In order to obtain desired effect, the dosage of the compound to be applied can vary with various factors, for example, the used compound, the protected crop, the type of harmful organism, the degree of infestation, the climatic conditions, the application method and the adopted formulation.

The dosage of compounds in the range of 10 g to 1000 g per hectare can provide a sufficient control.

An another object of the present invention also relates to a method for controlling phytopathogenic fungi in crops of farming and gardening and/or on domestic and breeding animals and/or environments frequented by human beings, by application of the compounds having general formula I. In particular, the dosage of compounds to be applied varies from 10 g to 1000 g per hectare.

For practical application in agriculture, it is usually beneficial to use compositions containing one or more compounds of general formula I.

Therefore, a further object of the present invention relates to fungicidal compositions containing one or more compounds having general formula I as active ingredient, the weight percentage of the active ingredient in the compositions is 0.1-99%.

Compositions can be used in the form of dry powders, wettable powders, emulsifiable concentrates, microemulsions, pastes, granulates, solutions, suspensions, etc,. The selection of the type of compositions depends on the specific application.

The compositions are prepared in the known method, for example by diluting or dissolving the active substance with a solvent medium and/or a solid diluent, optionally in the presence of surface-active agents.

Solid diluents or carriers which can be used are, for example: silica, kaolin, bentonite, talc, diatomite, dolomite, calcium carbonate, magnesia, chalk, clays, synthetic silicates, attapulgite, sepiolite.

Liquid diluents which can be used are, for example, besides water, aromatic organic solvents (xylols or mixtures of alkylbenzols, chlorobenzene, etc.), paraffins (petroleum fractions), alcohols (methanol, propanol, butanol, octanol, glycerin, etc.), esters (ethyl acetate, isobutyl acetate, etc.), ketones (cyclohexanone, acetone, acetophenone, isophorone, ethylamylketone, etc.), amides (N, N-dimethylformamide, N-methylpyrrolidone, etc.).

Surface-active agents which can be used are salts of sodium, calcium, triethylamine or triethanolamine of alkylsulfonates, alkylarylsulfonates, polyethoxylated alkylphenols, polyethoxylated esters of sorbitol, ligninsulfonates, etc.

The compositions can also contain special additives for particular purposes, for example adhesion agents such as Arabic gum, polyvinyl alcohol, polyvinyl-pyrrolidone, etc.

The concentration of active ingredient in the above compositions can vary within a wide range depending on the active compound, the applications for which they are destined, the environmental conditions and the type of adopted formulation. In general the concentration of active ingredient ranges from 0.1 to 99%, preferably from 5% to 60%.

If required, other active ingredients being compatible with the compounds having general formula I can be added to the compositions, such as, other acaricides/insecticides, fungicides, plant growth regulators, antibiotics, herbicides, fertilizers.

But for the form of compositions without being restricted thereby, also one or two or more composition can be mixed as active ingredient.

The preparation methods of several common formulation examples in the present invention are as follows:

The preparation of suspension concentrate: the common active component in formula is 5%-35%. With water as the medium, the compound in the invention, dispersing agent, suspending agent and antifreeze are added to sanding machine for grinding to make suspension concentrate.

The preparation of water emulsion: the compound in the invention, solvent and emulsifier are mixed together, to make a homogeneous oil phase. The water is mixed with antifreeze to make a homogeneous aqueous phase. In the high-speed stirring, the aqueous phase is added to the oil phase or oil phase is added to the aqueous phase, forming the water emulsion with good dispersity. The active component of water emulsions is generally 5%-15% in this invention. For the production of concentrated emulsions, the compounds of this invention are dissolved in one or more of the mixed solvent, and then emulsifier was added to enhance dispersion effects in the water.

The preparation of wettable powder: according to formulation requirements, the compound in the invention, surfactants and solid diluents are mixed well, after smashing through ultrafine pulverizer, that is the wettable powder products (for example, 10-60%). To prepare the spraying wettable powder, the compounds of this invention can form a mixture with solid powder, such as clay, inorganic silicates, carbonates, as well as wetting agents, adhesives and/or dispersant agent.

The preparation of water dispersible granules: the compound in the invention and powdered solid diluents, wetting agents and adhesives are mixed to smash, kneading together with water, added to the granulation certain mesh machine for granulation, then by drying and sieving (at the scope screen). Also, the compound, in the invention dispersants, disintegrants, wetting agents and solid diluent are added to sanding machine, grinding in water to produce suspension and then spray-drying granulation, usually the content of the prepared granular products is 20%-30%.

DESCRIPTION OF THE INVENTION IN DETAIL

The following examples are illustrative of the present invention, but without being restricted thereby. (except special explanation that all the materials can be purchased).

PREPARATION EXAMPLE Example 1 The Preparation of Intermediate (II-1)

1) The Preparation of Benzoxazine Ketone

To a solution of anthranilic acid 13.70 g (0.1 mol) in 150 mL tetrahydrofuran was added 19.80 g (0.067 mol) solid phosgene in batches at room temperature for 1.5 hours. Then the reaction mixture was continued stirring at room temperature for another 2-3 hours and monitored by TLC. After the reaction was over, the mixture was concentrated under reduced pressure, the residual was poured into 80 ml water and stirred until excessive phosgene was completely decomposed, the solid was then filtered, washed with 50 ml of water and 50 ml of petroleum ether successively, dried to give 14.00 g benzoxazine ketone as white solid with yield of 86.0%, m.p. 239-240° C.

2) The Preparation of 2-amino-N-methylbenzamide

To a solution of benzoxazine ketone 16.30 g (0.1 mol) in 150 mL acetonitrile was slowly dropwise added 40% methylamine aqueous solution at room temperature until the solid disappeared, about 80 ml methylamine aqueous solution was added. Then the reaction mixture was continued stirring at room temperature for another 0.5 hours and monitored by TLC. After the reaction was over, the mixture was concentrated under reduced pressure, the residual was filtered and washed with 50 ml of water and 50 ml of petroleum ether successively, then dried to give 13.73 g 2-amino-N-methylbenzamide as white solid with yield of 91.5%, m.p. 78-79° C.

3) The Preparation of 2-(2-chloroacetamido)-N-methylbenzamide

To a solution of 2-amino-N-methylbenzamide 15.00 g (0.1 mol) and triethylamine 12.10 g (0.12 mol) in 150 mL dichloromethane was added 12.40 g (0.11 mol) chloroacetyl chloride in 30 mL dichloromethane at room temperature for 0.5 hours. Then the reaction mixture was continued stirring at room temperature for another 2-3 hours and monitored by TLC. After the reaction was over, the mixture was concentrated under reduced pressure, the residual was filtered and washed with 50 ml of 10% diluted hydrochloric acid, 50 ml of saturated sodium bicarbonate solution, 50 ml of water and 50 ml of petroleum ether successively, then dried to give 18.90 g intermediate 2-(2-chloroacetamido)-N-methylbenzamide as white solid with yield of 83.4%, m.p. 155-157° C.

4) The Preparation of 2-(2-(4-cyanophenoxy)acetamido)-N-methylbenzamide (XII-1)

To a solution of 2-(2-chloroacetamido)-N-methylbenzamide 22.65 g (0.1 mol) and 4-hydroxybenzonitrile 14.29 g (0.12 mol) in 200 mL butanone was added 27.60 g (0.2 mol) potassium carbonate, then the reaction mixture was stirred and heated to reflux for 4-5 hours, and monitored by TLC until the reaction was over, the mixture was concentrated under reduced pressure and extracted with 300 mL of ethyl acetate to separate the organic phase, the organic phase was washed with 50 ml of 5% sodium hydroxide aqueous solution and 50 ml of brine successively, dried via anhydrous magnesium sulfate and evaporated, the residual was purified via silica gel column chromatography to obtain 25.00 g intermediate (XIII-1) as white solid with yield of 81.0%, m.p. 130-131° C.

5) The Preparation of 2-(2-(4-(aminomethyl)phenoxy)acetamido)-N-methylbenzamide (II-1)

To a solution of intermediate (XIII-1) 3.09 g (0.01 mol), Raney nickel (1.0 g) and 10 mL of 25% aqueous ammonia in 50 mL ethanol was filled with hydrogen, then the reaction mixture was continued stirring at room temperature for another 3-4 hours and monitored by TLC until the reaction was over, Raney nickel was filtered, the filtrate was concentrated under reduced pressure to give sticky liquid (II-1), which was cooled to give 2.16 g intermediate (II-1) as white solid with yield of 69.0%, m.p. 109-110° C.

Example 2 The Preparation of Intermediate (II-52)

1) The Preparation of 22-(4-acetylphenoxy)acetamido)-N-methylbenzamide

To a solution of 2-(2-chloroacetamido)-N-methylbenzamide 22.65 g (0.1 mol) and p-hydroxyacetophenone 16.32 g (0.12 mol) in 200 mL of butanone was added 27.60 g (0.2 mol) potassium carbonate. The mixture was stirred and heated to reflux for 4-5 hours, and monitored by TLC until the reaction was over, the reaction mixture was concentrated under reduced pressure and extracted with 300 mL of ethyl acetate to separate the organic phase, the organic phase was washed with 50 ml of 5% sodium hydroxide aqueous solution and 50 ml of brine successively, dried via anhydrous magnesium sulfate and evaporated, and the residual was purified via silica gel column chromatography to obtain 27.50 g 2-(2-(4-acetylphenoxy)acetamido)-N-methylbenzamide as white solid with yield of 84.4%, m.p. 252-253° C.

2) The Preparation of Oxime (XIV-1)

To a solution of 2-(2-(4-acetylphenoxy)acetamido)-N-methylbenzamide 1.60 g (0.005 mol) and hydroxylamine hydrochloride 0.63 g (0.0075 mol) in 30 mL of ethanol was dropwise added 1.38 g (0.01 mol) potassium carbonate in 3 mL of water at room temperature. The reaction mixture was stirred and heated to reflux for 4-5 hours, and monitored by TLC until the reaction was over, the mixture was concentrated under reduced pressure and extracted with ethyl acetate (30 mL) to separate the organic phase, the organic phase was washed with 20 ml of water and 20 ml of brine successively, dried via anhydrous magnesium sulfate and evaporated, and the residual was purified via silica gel column chromatography to obtain 27.50 g intermediate Oxime (XIV-1) as white solid with yield of 84.8%, m.p. 188-190° C.

3) The Preparation of Intermediate (II-52)

To a solution of intermediate (XIV-1) 3.41 g (0.01 mol), Raney nickel (2.0 g) and 12 mL of 25% aqueous ammonia in 50 mL ethanol was filled with hydrogen, then the reaction mixture was continued stirring at room temperature for 6-7 hours and monitored by TLC until the reaction was over, Raney nickel was filtered, the solution was concentrated under reduced pressure to give 2.56 g intermediate (II-52) as sticky liquid with yield of 78.3%.

Example 3 The Preparation of Intermediate (II-173)

1) The Preparation of tert-butyl-4-hydroxyphenylcarbamate

To a solution of p-aminophenol 10.9 g (0.1 mol), sodium bicarbonate 10.08 g (0.12 mol) and 150 mL water in 250 mL tetrahydrofuran was added di-tert-butyl dicarbonate 25.0 g (0.115 mol). The reaction mixture was continued stirring at room temperature for 24 hours, and monitored by TLC until the reaction was over, the mixture was concentrated under reduced pressure and extracted with ethyl acetate (500 mL) to separate the organic phase, the organic phase was washed with 50 ml of water and 50 ml of brine successively, dried via anhydrous magnesium sulfate and evaporated and the residual was purified via silica gel column chromatography to obtain 19.02 g tert-butyl-4-hydroxyphenylcarbamate as white solid with yield of 91.0%, m.p. 144-145° C.

¹HNMR: δ ppm 1.49 (9H, s), 5.08 (1H, s), 6.37 (1H, s), 6.74 (2H, d), 7.18 (2H, d).

2) The Preparation of Intermediate (XI-1)

To a solution of tert-butyl-4-hydroxyphenylcarbamate 6.27 g (0.03 mol) and 2-(2-chloroacetamido)-N-methylbenzamide 6.80 g (0.03 mol) in 100 mL butanone was added 8.30 g (0.06 mol) potassium carbonate. The reaction mixture was stirred and heated to reflux for 7-8 hours, and monitored by TLC until the reaction was over, the mixture was concentrated under reduced pressure and extracted with ethyl acetate (100 mL) to separate the organic phase, the organic phase was washed with 50 ml of water and 50 ml of brine successively, dried via anhydrous magnesium sulfate and evaporated and the residual was purified via silica gel column chromatography to obtain 10.05 g intermediate (XI-1) as white solid with yield of 84.0%, m.p. 142-143° C.

¹HNMR: δ ppm 1.61 (9H, s), 3.74 (3H, d), 5.14 (2H, s), 6.40 (1H, s), 6.98-7.01 (2H, d), 7.29 (2H, d), 7.47-7.50 (1H, m), 7.75-7.77 (2H, m), 8.30 (1H, d).

3) The Preparation of Intermediate (II-173)

To a solution of intermediate (XI-1) 3.99 g (0.01 mol) in 20 mL ethyl acetate was dropwise added 10 mL IN or 3N HCl. The reaction mixture was continued stirring at room temperature for 5-15 hours, and monitored by TLC until the reaction was over, filtered and the filter cake was washed with ethyl acetate to give 3.35 g intermediate (II-173) as white solid with yield of 99.8%, m.p. 239-240° C.

Example 4 The Preparation of Compound 15

To a solution of intermediate (II-1) 0.31 g (0.001 mol) and triethylamine 0.12 g (0.0012 mol) in 20 mL dichloromethane was dropwise added 4-chloro-1,3-dimethyl-1H-pyrazole-5-carbonyl formyl chloride (III-1) 0.21 g (0.0011 mol) in 10 mL dichloromethane. The reaction mixture was was continued stirring at room temperature for 1 hour, and monitored by TLC until the reaction was over, then the mixture was poured into 20 mL of water to separate the organic layer, the organic phase was washed with 10 ml of 5% diluted hydrochloric acid, 10 ml of saturated sodium bicarbonate solution and 10 ml of brine successively, dried via anhydrous magnesium sulfate and evaporated, the residual was purified via silica gel column chromatography to obtain 0.40 g compound 15 with yield of 81.5%, m.p. 157-158° C.

Example 5 The Preparation of Compound 16

Method 1:

To a solution of intermediate (II-1) 0.31 g (0.001 mol) and triethylamine 0.12 g (0.0012 mol) in mL dichloromethane was dropwise added 4-chloro-3-ethyl-1-methyl-1H-pyrazole-5-carbonyl formyl chloride (111-2) 0.23 g (0.0011 mol) in 10 mL dichloromethane. The reaction mixture was continued stirring at room temperature for 1 hour, and monitored by TLC until the reaction was over, then the mixture was poured into 20 mL of water to separate the organic layer, the organic phase was washed with 10 ml of 5% diluted hydrochloric acid, 10 ml of saturated sodium bicarbonate solution and 10 ml of brine successively, dried via anhydrous magnesium sulfate and evaporated, the residual was purified via silica gel column chromatography to obtain 0.41 g compound 16 with yield of 85.0%, m.p. 160-161° C.

Method 2:

1) The Preparation of Intermediate (VIII-2)

To a solution of 4-(aminomethyl)phenol 1.23 g (0.01 mol) and triethylamine 1.2 g (0.012 mol) in 50 mL dichloromethane was dropwise added 4-chloro-3-ethyl-1-methyl-1H-pyrazole-5-carbonyl formyl chloride (III-2) 2.3 g (0.011 mol) in 30 mL dichloromethane. The reaction mixture was continued stirring at room temperature for 4-5 hour, and monitored by TLC until the reaction was over, then the mixture was poured into 50 mL of water to separate the organic layer, the organic phase was washed with 10 ml of 5% diluted hydrochloric acid, 10 ml of saturated sodium bicarbonate solution and 10 ml of brine successively, dried via anhydrous magnesium sulfate and evaporated, the residual was purified via silica gel column chromatography to obtain 2.50 g intermediate (VIII-2) with yield of 85.2%, m.p. 167-168° C.

2) The Preparation of Compound 16

To a solution of intermediate (VIII-2) 0.30 g (0.001 mol) and potassium carbonate 0.17 g (0.0012 mol) in 30 mL N,N-dimethylformamide was added intermediate (VI-1) 0.27 g (0.0011 mol) to react at room temperature for 1 hour, then continuely stirred and heated to reflux for 7-8 hours, and monitored by TLC until the reaction was over, the mixture was concentrated under reduced pressure and poured into 20 mL of water, then extracted with ethyl acetate (100 mL) to separate the organic layer, the organic phase was washed with 10 ml of brine, dried via anhydrous magnesium sulfate and evaporated, the residual was purified via silica gel column chromatography to obtain 0.32 g compound 16 with yield of 66.0%, m.p. 160-161° C.

Example 6 The Preparation of Compound 41

To a solution of intermediate (II-52) 0.33 g (0.001 mol) and triethylamine 0.12 g (0.0012 mol) in 20 mL dichloromethane was dropwise added 4-chloro-3-ethyl-1-methyl-1H-pyrazole-5-carbonyl formyl chloride (III-2) 0.23 g (0.0011 mol) in 10 mL dichloromethane. The reaction mixture was continued stirring at room temperature for 1 hour, and monitored by TLC until the reaction was over, then the mixture was poured into 20 mL of water to separate the organic layer, the organic phase was washed with 10 ml of 10% diluted hydrochloric acid, 10 ml of saturated sodium bicarbonate solution and 10 ml of brine successively, dried via anhydrous magnesium sulfate and evaporated, the residual was purified via silica gel column chromatography to obtain 0.43 g compound 41 with yield of 89.7%, m.p. 138-139° C.

Example 7 The Preparation of Compound 202

To a solution of intermediate (II-173) 0.34 g (0.001 mol) and triethylamine 0.22 g (0.0022 mol) in 20 mL dichloromethane was dropwise added 4-chloro-1,3-dimethyl-1H-pyrazole-5-carbonyl formyl chloride (III-1) 0.21 g (0.0011 mol) in 10 mL dichloromethane. The reaction mixture was continued stirring at room temperature for 1 hour, and monitored by TLC until the reaction was over, then the mixture was poured into 20 mL of water to separate the organic layer, the organic phase was washed with 10 ml of 10% diluted hydrochloric acid, 10 ml of saturated sodium bicarbonate solution and 10 ml of brine successively, dried via anhydrous magnesium sulfate and evaporated, the residual was purified via silica gel column chromatography to obtain 0.42 g compound 202, yield (92.2%), m.p. 182-183° C.

Other compounds of the general formula (I) were prepared according to the above examples.

Melting point (Melting point meter not corrected) and ¹HNMR spectrum (¹HNMR, 300 MHz, internal standard: TMS, solvent CDCl₃) of some compounds of this invention are as follows:

Compound 2: m.p. 173-174° C. δ ppm 2.23 (3H, s), 3.73 (3H, s), 4.12 (3H, s), 4.49-4.51 (2H, m), 5.19 (2H, s), 6.26 (1H, s), 7.02-7.05 (2H, m), 7.25-7.28 (2H, m), 7.50-7.55 (1H, m), 7.70-7.74 (2H, m), 8.28-8.33 (1H, m).

Compound 3: m.p. 147-148° C. δ ppm 1.23 (3H, t), 2.56-2.61 (2H, m), 3.73 (3H, s), 4.12 (3H, s), 4.50 (2H, d), 5.18 (2H, s), 6.28 (1H, s), 7.02-7.07 (2H, m), 7.26-7.29 (2H, m), 7.51-7.54 (1H, m), 7.69-7.76 (2H, m), 8.27-8.30 (1H, m).

Compound 4: m.p. 172-174° C. δ ppm 0.99 (3H, t), 1.66-1.69 (2H, m), 2.55 (2H, t), 3.73-3.78 (6H, m), 4.54 (2H, d), 5.17 (2H, s), 6.59 (1H, s), 7.00-7.03 (3H, m), 7.27-7.32 (2H, m), 7.48-7.52 (1H, m), 7.70-7.74 (2H, m), 8.28-8.32 (1H, m).

Compound 7: m.p. 126-128° C. δ ppm 0.95 (6H, d), 1.83-1.87 (1H, m), 2.46 (2H, d), 3.72-3.74 (6H, m), 4.54 (2H, d), 5.16 (2H, s), 6.57 (1H, s), 7.00-7.03 (2H, m), 7.10 (1H, s), 7.28-7.31 (2H, m), 7.48-7.52 (1H, m), 7.71-7.76 (2H, m), 8.27-8.30 (1H, m).

Compound 8: m.p. 124-125° C. δ ppm 0.87-0.89 (2H, m), 1.03-1.06 (2H, m), 1.61 (1H, m), 3.73 (3H, s), 3.85 (3H, s), 4.53 (2H, d), 5.17 (2H, s), 7.00-7.03 (3H, m), 7.28-7.31 (2H, m), 7.49-7.52 (1H, m), 7.71-7.76 (2H, m), 8.28-8.32 (1H, m).

Compound 14: m.p. 159-161° C. δ ppm 3.74 (3H, s), 4.22 (3H, s), 4.53-4.55 (2H, m), 5.19 (2H, s), 6.30 (1H, s), 6.72 (1H, s), 7.04-7.07 (2H, m), 7.26-7.36 (6H, m), 7.49-7.52 (1H, m), 7.65-7.77 (4H, m), 8.26-8.30 (1H, m).

Compound 15: m.p. 157-158° C. δ ppm 2.22 (3H, s), 3.74 (3H, s), 4.13 (3H, s), 4.57 (2H, d), 5.20 (2H, s), 7.04-7.07 (3H, m), 7.27-7.32 (2H, m), 7.50-7.54 (1H, m), 7.73-7.77 (2H, m), 8.28-8.31 (1H, m).

Compound 16: m.p. 160-161° C. δ ppm 1.23 (3H, t), 2.59-2.66 (2H, m), 3.76 (3H, s), 4.13 (3H, s), 4.57 (2H, d), 5.26 (2H, s), 7.06-7.08 (4H, m), 7.27-7.33 (2H, m), 7.52-7.56 (1H, m), 7.78-7.79 (2H, m), 8.29-8.32 (1H, m).

Compound 17: m.p. 122-123° C. δ ppm 0.96 (3H, t), 1.60-1.62 (2H, m), 2.64 (2H, t), 3.73 (3H, s), 3.78 (3H, s), 4.54 (2H, d), 5.17 (2H, s), 7.01-7.04 (3H, m), 7.27-7.33 (2H, m), 7.49-7.53 (1H, m), 7.72-7.77 (2H, m), 8.28-8.31 (1H, m).

Compound 20: m.p. 119-120° C. δ ppm 0.95 (6H, d), 1.90-2.00 (1H, m), 2.51 (2H, d), 3.73 (3H, s), 3.77 (3H, s), 4.54 (2H, d), 5.17 (2H, s), 7.00-7.03 (3H, m), 7.28-7.33 (2H, m), 7.48-7.52 (1H, m), 7.71-7.72 (2H, m), 8.28-8.32 (1H, m).

Compound 26: m.p. 158-159° C. δ ppm 2.23 (3H, s), 3.74 (3H, s), 4.13 (3H, s), 4.57 (2H, d), 5.19 (2H, s), 7.04-7.07 (3H, m), 7.27-7.33 (2H, m), 7.51-7.55 (1H, m), 7.71-7.72 (2H, m), 8.28-8.32 (1H, m).

Compound 36: m.p. 100-102° C. δ ppm 1.25 (3H, t), 3.00-3.02 (2H, m), 3.64 (3H, s), 3.84 (3H, s), 4.38 (2H, d), 5.22 (2H, s), 7.03-7.05 (2H, m), 7.28-7.31 (2H, m), 7.43-7.47 (1H, m), 7.61-7.65 (1H, m), 7.66-7.70 (1H, m), 8.16-8.20 (1H, m), 8.82 (1H, s).

Compound 41: m.p. 138-139° C. δ ppm 1.25 (3H, t), 1.57 (3H, d), 1.80-1.84 (1H, m), 2.58-2.66 (2H, m), 3.73 (3H, s), 4.09 (3H, s), 5.18-5.23 (2H, m), 6.96 (1H, d), 7.04-7.07 (2H, m), 7.27-7.34 (2H, m), 7.48-7.53 (1H, m), 7.69-7.76 (2H, m), 8.28-8.30 (1H, m).

Compound 46: m.p. 139-141° C. δ ppm 1.22 (3H, t), 1.55 (3H, d), 2.58-2.66 (2H, m), 3.20 (3H, s), 4.12 (3H, d), 4.93-4.97 (2H, m), 5.16-5.20 (1H, m), 6.63 (1H, d), 6.80-6.87 (3H, m), 6.92-6.95 (1H, m), 7.23-7.29 (4H, m), 7.88-7.91 (1H, m).

Compound 62: m.p. 120-122° C. δ ppm 1.21 (3H, t), 1.84 (3H, d), 2.52-2.60 (2H, m), 2.84 (2H, t), 3.60-3.66 (2H, m), 3.72 (3H, s), 4.09 (3H, s), 5.49-5.61 (1H, m), 6.65 (1H, s), 6.96 (2H, d), 7.14 (2H, d), 7.42-7.55 (1H, m), 7.69-7.81 (2H, m), 8.22-8.31 (1H, m).

Compound 66: m.p. 135-137° C. δ ppm 1.22 (3H, t), 1.85 (3H, d), 2.57-2.65 (2H, m), 3.75 (3H, s), 4.11 (3H, s), 4.54 (2H, d), 5.53-5.55 (1H, m), 6.97-7.00 (2H, m), 7.24-7.27 (2H, m), 7.49-7.51 (1H, m), 7.72-7.76 (2H, m), 8.25-8.28 (1H, m).

Compound 69: m.p. 138-139° C. δ ppm 1.22 (3H, t), 1.68 (3H, d), 2.57-2.66 (2H, m), 2.91 (3H, d), 4.09 (3H, s), 4.54 (2H, d), 4.75-4.77 (1H, m), 6.50 (1H, s), 6.99-7.07 (4H, m), 7.26-7.29 (2H, m), 7.39-7.44 (2H, m), 8.55-8.59 (1H, m), 11.85 (1H, s).

Compound 77: m.p. 186-187° C. δ ppm 2.08 (3H, s), 2.16 (3H, s), 3.74 (3H, d), 4.01 (3H, s), 4.57 (2H, d), 6.00 (2H, s), 7.04-7.07 (3H, m), 7.50-7.54 (2H, m), 7.72-7.74 (2H, m), 8.23-8.27 (1H, m).

Compound 78: m.p. 114-116° C. δ ppm 1.84 (3H, d), 2.16 (3H, s), 2.84 (2H, t), 3.65 (2H, t), 3.68 (3H, s), 4.07 (3H, s), 5.51-5.55 (2H, m), 6.63 (1H, s), 6.96 (2H, d), 7.14 (2H, d), 7.43-7.50 (1H, t), 7.62-7.80 (2H, m), 8.26 (1H, d).

Compound 94: m.p. 166-168° C. δ ppm 1.37 (3H, t), 2.24 (3H, s), 2.29 (3H, s), 4.13 (3H, s), 4.31-4.33 (2H, m), 4.60 (2H, d), 4.67 (2H, s), 7.03-7.05 (3H, m), 7.23-7.27 (2H, m), 7.33-7.36 (2H, m), 7.42-7.45 (1H, m), 7.80-7.83 (1H, m), 9.83 (1H, s).

Compound 95: m.p. 170-171° C. δ ppm 1.41 (3H, t), 2.23 (3H, s), 4.14 (3H, s), 4.40-4.42 (2H, m), 4.59 (2H, d), 4.65 (2H, s), 7.07-7.14 (5H, m), 7.33-7.35 (2H, m), 7.57-7.60 (1H, m), 8.08 (1H, m), 8.80 (1H, m).

Compound 99: m.p. 211-212° C. δ ppm 1.24 (3H, t), 1.39 (3H, t), 2.62-2.64 (2H, m), 4.15 (3H, s), 4.40-4.43 (2H, m), 4.59 (2H, d), 4.65 (2H, s), 7.07-7.14 (5H, m), 7.33-7.35 (2H, m), 7.57 (1H, m), 8.08 (1H, m), 8.78-8.82 (1H, m).

Compound 104: m.p. 178-180° C. δ ppm 1.42 (3H, t), 2.24 (3H, s), 3.74 (3H, s), 4.50-4.54 (4H, m), 5.19 (2H, s), 6.23 (2H, d), 7.03-7.06 (2H, m), 7.26-7.29 (3H, m), 7.52 (1H, t), 7.70-7.74 (2H, m), 8.23-8.27 (1H, m).

Compound 105: m.p. 138-139° C. δ ppm 1.24 (3H, t), 1.41 (3H, t), 2.59-2.67 (2H, m), 3.74 (3H, s), 4.52-4.59 (4H, m), 5.19 (2H, s), 6.97 (1H, s), 7.04-7.07 (2H, m), 7.19-7.32 (3H, m), 7.49-7.54 (1H, m), 7.69-7.87 (2H, m), 8.28-8.31 (1H, m).

Compound 107: m.p. 137-138° C. δ ppm 1.38 (3H, t), 2.26-2.27 (3H, s), 3.73 (3H, s), 4.02-4.09 (2H, m), 4.54 (2H, d), 5.17 (2H, s), 7.01-7.05 (3H, m), 7.27-7.33 (2H, m), 7.50-7.53 (1H, m), 7.69-7.76 (2H, m), 8.27-8.31 (1H, m).

Compound 108: m.p. 144-145° C. δ ppm 1.23 (3H, t), 1.41 (3H, t), 2.59-2.64 (2H, m), 3.74 (3H, s), 4.52-4.58 (4H, m), 5.19 (2H, s), 6.90 (1H, s), 7.04-7.07 (2H, m), 7.26-7.32 (3H, m), 7.49-7.53 (1H, m), 7.69-7.76 (2H, m), 8.28-8.31 (1H, m).

Compound 117: m.p. 172-174° C. δ ppm 3.61 (3H, s), 4.27 (2H, d), 5.21 (2H, s), 7.00-7.03 (2H, m), 7.16-7.21 (3H, m), 7.52-7.65 (3H, m), 7.76-7.79 (1H, m), 8.07-8.15 (2H, m), 8.45-8.47 (1H, m), 9.11-9.15 (1H, m).

Compound 118: m.p. 118-120° C. δ ppm 2.62 (3H, s), 3.73 (3H, s), 4.42 (2H, d), 5.21 (2H, s), 6.46 (1H, s), 6.70 (1H, s), 7.02 (2H, d), 7.21 (2H, d), 7.37-7.42 (1H, m), 7.76 (1H, s), 7.86-7.92 (1H, d), 8.43 (1H, s).

Compound 121: m.p. 141-143° C. δ ppm 2.59 (3H, s), 3.72 (3H, s), 4.43 (2H, d), 5.19 (2H, s), 6.36 (1H, s), 6.71 (1H, s), 7.03 (2H, d), 7.19 (2H, d), 7.38-7.43 (1H, m), 7.72 (1H, s), 7.90 (1H, d), 8.25 (1H, s), 8.44 (1H, d).

Compound 129: m.p. 225-226° C. δ ppm 3.72 (3H, s), 4.49 (2H, d), 5.22 (2H, s), 7.03-7.06 (2H, m), 7.14-7.18 (1H, m), 7.28-7.31 (2H, m), 7.50-7.55 (1H, m), 7.67-7.78 (3H, m), 8.22-8.24 (1H, m), 8.70 (1H, s), 14.00 (1H, s).

Compound 141: m.p. 118-119° C. δ ppm 1.24 (3H, t), 1.42 (3H, t), 2.59-2.66 (2H, m), 4.14 (3H, s), 4.25-4.29 (2H, m), 4.58 (2H, d), 5.19 (2H, s), 7.05-7.08 (3H, m), 7.26-7.34 (2H, m), 7.48-7.49 (1H, m), 7.73-7.76 (1H, m), 7.91-7.94 (1H, m).

Compound 147: m.p. 138-140° C. δ ppm 2.23 (3H, s), 3.02 (6H, d), 4.14 (3H, s), 4.58-4.60 (4H, m), 7.01-7.04 (3H, m), 7.12-7.17 (1H, m), 7.25-7.34 (4H, m), 7.40-7.46 (1H, m), 10.00 (1H, s).

Compound 148: m.p. 117-119° C. δ ppm 1.23 (3H, t), 2.62-2.64 (2H, m), 2.97-3.04 (6H, m), 4.14 (3H, s), 4.58-4.60 (4H, m), 7.01-7.13 (4H, m), 7.25-7.34 (4H, m), 7.40-7.44 (1H, m), 8.34 (1H, d), 9.98 (1H, s).

Compound 156: m.p. 234-236° C. δ ppm 2.23 (3H, s), 4.14 (3H, s), 4.58-4.60 (2H, m), 5.09 (2H, s), 7.00-7.09 (3H, m), 7.26-7.35 (1H, m), 7.49-7.54 (2H, m), 7.68-7.83 (2H, m), 8.27-8.29 (1H, m), 9.70 (1H, s).

Compound 157: m.p. 237-238° C. δ ppm 1.23 (3H, t), 2.59-2.64 (2H, m), 4.13 (3H, s), 4.54-4.60 (2H, m), 5.47 (2H, d), 7.00-7.08 (3H, m), 7.26-7.35 (1H, m), 7.46-7.61 (2H, m), 7.71-7.83 (3H, m), 8.17-8.34 (2H, m).

Compound 162: m.p. 140-142° C. δ ppm 1.66 (3H, s), 2.22 (3H, s), 3.72 (3H, s), 4.12 (3H, s), 4.57 (2H, d), 5.21 (1H, s), 7.06 (1H, s), 7.09 (2H, d), 7.30 (2H, d), 7.38 (1H, t), 7.59 (1H, d), 8.12 (1H, d).

Compound 166: m.p. 177-178° C. δ ppm 2.22 (3H, s), 2.58 (3H, s), 3.72 (3H, s), 4.13 (3H, s), 4.57 (2H, d), 5.18 (2H, s), 6.97 (1H, s), 7.06 (2H, d), 7.30 (2H, d), 7.69 (1H, s), 8.26 (1H, d).

Compound 167: m.p. 184-186° C. δ ppm 2.23 (3H, s), 2.62 (3H, s), 3.74 (3H, s), 4.13 (3H, s), 4.57 (2H, d), 5.22 (1H, s), 7.01 (1H, s), 7.06 (2H, d), 7.29 (2H, d), 7.78 (1H, s), 8.46 (1H, s).

Compound 169: m.p. 157-159° C. δ ppm 2.15 (3H, s), 3.62 (3H, s), 3.97 (3H, s), 4.33 (2H, d), 5.20 (2H, s), 6.58 (1H, s), 7.00-7.03 (2H, m), 7.22-7.25 (2H, m), 7.69-7.71 (1H, m), 7.76-7.78 (2H, m), 8.73-8.77 (1H, m).

Compound 170: m.p. 152-153° C. δ ppm 1.22 (3H, t), 2.58-2.66 (5H, m), 3.73 (3H, s), 4.14 (3H, s), 4.57 (2H, d), 5.23 (2H, s), 6.98 (1H, s), 7.07-7.09 (2H, m), 7.26-7.32 (3H, m), 7.39-7.41 (1H, d), 8.18 (1H, d).

Compound 171: m.p. 143-144° C. δ ppm 2.22 (3H, s), 2.62 (3H, s), 3.73 (3H, s), 4.13 (3H, s), 4.57 (2H, d), 5.22 (2H, s), 7.01 (1H, s), 7.06-7.09 (2H, m), 7.26-7.32 (2H, m), 7.36-7.41 (1H, m), 7.59 (1H, d), 8.12 (1H, d).

Compound 172: m.p. 154-155° C. δ ppm 1.23 (3H, t), 2.58 (3H, s), 2.61-2.66 (2H, m), 3.73 (3H, s), 4.13 (3H, s), 4.57 (2H, d), 5.21 (2H, s), 6.99 (1H, s), 7.04-7.07 (2H, m), 7.27-7.32 (2H, m), 7.53-7.54 (1H, m), 8.08-8.09 (1H, m).

Compound 177: m.p. 107-108° C. δ ppm 1.26 (3H, t), 2.25 (3H, s), 2.63 (3H, s), 4.14 (3H, s), 4.26-4.28 (2H, m), 4.48-4.52 (2H, m), 5.23 (2H, s), 6.31 (1H, s), 7.06-7.09 (2H, m), 7.27 (2H, m), 7.37-7.42 (1H, m), 7.59-7.61 (1H, m), 8.12-8.14 (1H, m).

Compound 178: m.p. 139-140° C. δ ppm 1.23 (3H, t), 1.36 (3H, t), 2.29 (3H, s), 2.59-2.67 (2H, m), 4.13 (3H, s), 4.28-4.35 (2H, m), 4.59 (2H, d), 4.67 (2H, s), 7.02-7.05 (3H, m), 7.19-7.26 (1H, m), 7.33-7.36 (2H, m), 7.42-7.45 (1H, m), 7.80-7.82 (1H, m), 9.85 (1H, s).

Compound 186: m.p. 144-146° C. δ ppm 2.19 (3H, s), 2.87 (2H, t), 3.64-3.71 (2H, m), 3.75 (3H, s), 4.10 (3H, s), 5.18 (2H, s), 6.67 (1H, s), 7.02 (2H, d), 7.19 (2H, d), 7.49-7.54 (1H, m, 7.70-7.77 (2H, m), 8.29-8.31 (1H, s).

Compound 187: m.p. 145-146° C. δ ppm 1.22 (3H, t), 2.55-2.62 (2H, m), 2.87 (2H, t), 3.65-3.71 (2H, m), 3.75 (3H, s), 4.10 (3H, s), 5.18 (2H, s), 6.68 (1H, s), 7.02 (2H, d), 7.19 (2H, d), 7.49-7.54 (1H, m), 7.70-7.79 (2H, m), 8.29-8.31 (1H, s).

Compound 194: m.p. 136-138° C. δ ppm 1.87-1.97 (2H, m), 2.22 (3H, d), 2.67 (2H, t), 3.42-3.49 (2H, m), 3.60 (3H, s), 4.11 (3H, s), 5.16 (2H, s), 6.70 (1H, s), 6.98 (2H, d), 7.13 (2H, d), 7.48-7.53 (1H, m, 7.70-7.76 (2H, m), 8.28-8.31 (1H, s).

Compound 195: oil. δ ppm 2.23 (3H, s), 3.26-3.79 (8H, s), 4.13 (3H, s), 4.58 (2H, d), 4.61 (2H, s), 7.01 (3H, t), 7.168 (1H, t), 7.22 (1H, t), 7.33 (1H, d), 7.43 (1H, t), 8.35 (1H, d), 9.85 (1H, s).

Compound 199: m.p. 170-171° C. δ ppm 1.89-1.94 (2H, m), 2.04 (3H, s), 2.13 (3H, d), 2.66 (2H, t), 3.42-3.49 (2H, m), 3.74 (3H, s), 3.98 (3H, s), 5.16 (2H, s), 5.72 (1H, s), 6.99 (2H, d), 7.13 (2H, d), 7.51-7.53 (1H, m), 7.69-7.76 (2H, m), 8.28-8.31 (1H, m).

Compound 202: m.p. 182-183° C. δ ppm 2.27 (3H, s), 3.75 (3H, d), 4.16 (3H, s), 5.20 (2H, s), 7.08-7.12 (2H, m), 7.54-7.72 (6H, m), 8.32-8.36 (2H, m).

Compound 220: m.p. 175-177° C. δ ppm 2.18 (3H, s), 2.78 (3H, d), 3.84 (3H, s), 4.40 (2H, d), 4.65 (2H, s), 6.96 (2H, d), 7.28 (2H, d), 7.34 (1H, t), 7.49 (1H, d), 7.80 (1H, d), 8.04 (1H, s), 8.31 (1H, d), 8.63 (1H, t), 8.36 (1H, s), 10.14 (1H, s).

Compound 300: m.p. 188-190° C. δ ppm 1.39 (3H, t), 2.23 (3H, s), 4.14 (3H, s), 4.34-4.38 (2H, m), 4.59-4.63 (2H, m), 6.98-7.01 (2H, m), 7.34-7.37 (2H, m), 7.67-7.70 (2H, m), 8.04-8.06 (2H, m), 8.40 (1H, s).

Compound 304: m.p. 168-170° C. δ ppm 1.23 (3H, t), 1.40 (3H, t), 2.62-2.64 (2H, m), 4.15 (3H, s), 4.36-4.40 (2H, m), 4.60-4.63 (4H, m), 6.99-7.02 (2H, m), 7.34-7.37 (2H, m), 7.40-7.42 (1H, m), 7.80-7.81 (1H, m), 8.04-8.05 (2H, m), 8.38 (1H, s).

Compound 504: m.p. 185-186° C. δ ppm 1.40 (3H, t), 2.24 (3H, s), 4.14 (3H, s), 4.36-4.43 (2H, m), 4.60-4.63 (4H, m), 6.99-7.02 (3H, m), 7.34-7.37 (2H, m), 7.42-7.48 (1H, m), 7.83-7.86 (1H, m), 8.02-8.04 (2H, m), 8.37 (1H, s).

Compound 509: m.p. 172-173° C. δ ppm 1.23 (3H, t), 1.39 (3H, t), 2.59-2.64 (2H, m), 4.14 (3H, s), 4.34-4.41 (2H, m), 4.59-4.63 (4H, m), 6.98-7.01 (3H, m), 7.34-7.37 (2H, m), 7.67-7.70 (2H, m), 8.03-8.06 (2H, m), 8.41 (1H, s).

FORMULATION EXAMPLE Base on 100% Active Ingredient (Weight/Weight %) Example 8 30% Wettable Powders

Compound 15 30%  Sodium dodecyl sulfate 2% Lignin sulfonate 3% Naphthalene sulfonic acid formaldehyde condensate 5% Precipitated calcium carbonate Make up to 100%

Compound 15 and other components are fully mixed, after smashing through ultrafine pulverizer, 30% compound 15 wettable powders products were obtained.

Example 9 20% Suspension Concentrate

Compound 15 20%  Glycol 5% Nonylphenols polyethylene glycol ether 3% Lignin sulfonate 5% Carboxymethyl cellulose 1% 75% of silicone oil water emulsion 0.4%  Water Make up to 100%

Fully mixing compound 15 and other components, suspension concentrate can be obtained, and then any required concentration dilution can be obtained by diluting the above obtained concentrated suspension with water.

Example 10 60% Water Dispersible Granules

Compound 16 60%  Naphthalene sulfonate formaldehyde condensate 12%  N-methyl-N-oil acyl - bovine sodium 8% Polyvinylpyrrolidone 2% Carboxymethyl cellulose 2% Kaolin Make up to 100%

To mix compound 16 and other components, after smashing, kneading together with water, added to the granulation 10-100 mesh machine for granulation, then by drying and sieving (at the scope screen).

Test of Biological Activity Example 11 Determination of Greenhouse Biological Activity (Cucumber Downy Mildew)

The tests were carried out with the method of pot seedling assay. The compounds of the present invention were diluted to given concentrations and sprayed on the leaves of cucumber seedling at the same stage, on which growing point were cut off and two euphyllas were kept, meanwhile, water were set as the blank control, 3 replicates were set for each treatment. Cucumber downy mildew spore suspension were inoculated on the second day after treatment, then, the plants were placed in a chamber (temperature: day 25° C., and night 20° C., relative humidity 95 to 100%), and then placed in greenhouse (25±2° C.) 24 hours later and routine management was conducted. The test results were investigated 5 days later, disease classification refers to the national standard of the People's Republic of China—“Pesticide-Guidelines for The Field Efficacy Trials”, the control effect was calculated by disease index.

Some of the test results are as follows:

At 400 ppm, compounds 2, 3, 15, 16, 66, 69 and 177 showed 100% control of cucumber downy mildew.

At 50 ppm, compounds 2, 3, 15, 16 and 177 showed 100% control of cucumber downy mildew.

At 25 ppm, compounds 15, 16 and 177 showed 100% control of cucumber downy mildew. compound 3 showed 95% control of cucumber downy mildew, compound 2 showed 75% control of cucumber downy mildew.

The comparative test was carried out against cucumber downy mildew between compound 15 of the present invention and three contrasts Dimethomorph, famoxadone and metalaxyl(tech. commercially available), the test results were listed in table 18.

TABLE 18 Control (%) Compd. 100 ppm 50 ppm 25 ppm 12.5 ppm 6.25 ppm Compd. 15 100 96 88 66 44 dimethomorph 100 88 85 74 29 famoxadone 81 74 51 22 14 metalaxyl 59 29 22 7 0 untreated control (disease index) 100

The persistence comparative test was carried out against cucumber downy mildew between compound 15 of the present invention and Dimethomorph, the test results were listed in table 19.

TABLE 19 Control (%) the days after 400 200 100 treatment Compd. ppm ppm ppm 50 ppm 25 ppm 3 Compd. 15 100 100 96 74 52 dimethomorph 100 74 44 30 0 7 Compd. 15 81 74 70 62 44 dimethomorph 74 44 0 0 0 untreated control inoculation on the 3th, 7th days after treatment: (disease index) 100

Example 12 Determination of Greenhouse Biological Activity (Wheat Powdery Mildew)

The tests were carried out with the method of pot seedling assay. The compounds of the present invention were diluted to given concentrations and sprayed on the leaves of wheat seedling at the same two-leaf stage, meanwhile, water were set as the blank control, 3 replicates were set for each treatment. Wheat powdery mildew spore suspension were inoculated on the second day after treatment, and then placed in greenhouse (25±2° C.) and routine management was conducted. The test results were investigated on 8th day, Disease grading refers to the National Standard of the People's Republic of China—“Pesticide-Guidelines for The Field Efficacy Trials”, the control effect was calculated by disease index.

Some of the test results are as follows:

At 400 ppm, compounds 2, 3, 15, 16 and 177 showed 100% control of wheat powdery mildew.

Example 13 Determination of Greenhouse Biological Activity (Corn Rust)

The tests were carried out with the method of pot seedling assay. The compounds of the present invention were diluted to given concentrations and sprayed on the leaves of corn seedling at the same two-leaf stage, meanwhile, water were set as the blank control, 3 replicates were set for each treatment. Corn rust spore suspension were inoculated on the second day after treatment, then, the plants were placed in an environmental chamber (temperature: day 25° C., and night 20° C., relative humidity 95 to 100%), and then placed in greenhouse (25±2° C.) 24 hours later, routine management was conducted. The test results were investigated on 8th day, disease grading refers to the National Standard of the People's Republic of China—“Pesticide-Guidelines for The Field Efficacy Trials”, the control effect was calculated by disease index.

Some of the test results are as follows:

At 400 ppm, compounds 2, 3, 15, 16, 17, 66, 69, 94, 95, 99, 156, 177 showed 100% control of corn rust.

At 25 ppm, compound 15 showed 100% control of corn rust.

The comparative test was carried out against corn rust between compound 15 of the present invention and Epoxiconazole (tech. commercially available), the test results were listed in table 20.

TABLE 20 Control (%) 6.25 3.13 Compd. 100 ppm 50 ppm 25 ppm 12.5 ppm ppm ppm Compd. 15 100 100 95 80 60 20 epoxiconazole 100 100 95 90 75 40 untreated (disease index) 100 control

Example 14 Determination of Greenhouse Biological Activity In Vitro (Rice Blast Etc.)

The tests were carried out with the method of spore germination. According to the design concentration, the compounds of the present invention were added into the cells of 96 cells culture plates, then rice blast spore suspension was dropped into the cells, meanwhile, water were set as the blank control, 3 replicates were set for each treatment. the treated culture plates were placed in an incubator (temperature: 24° C. to 26° C.), The test results were investigated on the second day after treatment, and the spore germinations rate were calculated.

Some of the test results are as follows:

At 25 ppm, compounds 2, 3, 15, 16, 95 and 177 showed 100% inhibition ratio on spore germination of rice blast.

At 0.3 ppm, compound 15 showed 100% inhibition ratio on spore germination of rice blast.

Example 15 Determination of Greenhouse Biological Activity In Vitro (Rice Sheath Blight Etc.)

Referring to the determination method of activity in vitro above, lots of inhibition activity tests of compound 15 against many fungus were carried out, and the test results are as follows: Compound 15 has good activity against rice sheath blight, mango anthracnose, sigatoka, corn southern leaf blight, banana anthracnose and so on, with EC₅₀ values of 0.799, 1.518, 2.389, 0.035, 2.867 ppm respectively.

Example 16

Biological activities in greenhouse of compound 15 and some intermediates of this invention against cucumber downy mildew, wheat powdery mildew and corn rust at 400 ppm were listed in table 21. The method was mentioned before.

TABLE 21 compound or cucumber downy wheat powdery Intermediate mildew mildew corn rust Compd. 15 100 100 100 VI-1 0 0 0 VI-54 30 0 0 VI-20 0 0 0 VI-56 75 0 30 VIII-1 95 0 50 VIII-138 0 0 0 VIII-139 0 0 0 II-1 0 100 0

The structure of each intermediate is as follows:

Example 17 Field Trials Against Cucumber Downy Mildew

The trial was carried out in a greenhouse in July 2011 in Yangling district, Shanxi Province. Before the treatment, the cucumber plants were at the beginning of infection. The trial method was based on the National Standard of the People's Republic of China—“Pesticide-Guidelines for The Field Efficacy Trials”. The concentrations of Compound 15 (20% SC of Example 9, the same below) of this invention were 400 ppm, 200 ppm and 100 ppm. Chlorothalonil 75% WP and dimethomorph 50% WP (standards, both commercially available) were respectively 800 ppm and 200 ppm. The Area of plot was 15 m², random arrangement and 3 times replication. The volume was about 600 L/hm², and water was as the control. The results of Compound 15 on cucumber downy mildew in field were listed in table 22.

TABLE 22 Treatment Control (%) Compd. concentration(ppm) I II III average Compd. 15 400 80 81 86 82 200 60 65 72 66 100 33 53 69 52 dimethomorph 200 44 52 63 53 chlorothalonil 800 68 73 81 74 untreated control (disease index) (58) (52) (42) (51)

Example 18 Field Trials Against Rice Blast

The trial was carried out in a rice field on Shuguang farm of Heilongjiang Province in July 2011. Before the first treatment the rice was at the end of pregnancy, and on the second treatment, the rice was at heading stage. The trial method was based on the National Standard of the People's Republic of China—“Pesticide-Guidelines for The Field Efficacy Trials”. The concentrations of Compound 15 of this invention were 800 ppm, 600 ppm and 400 ppm. Fluazinam 50% SC (standard, commercially available) was 600 ppm. The Area of plot was 30 m², random arrangement and 3 times replication. The volume was about 600 L/hm², and water was as the control. The results of Compound 15 on cucumber downy mildew in field were listed in table 23.

TABLE 23 Treatment Control (%) Compd. concentration(ppm) I II III average Compd. 15 800 84 89 88 87 600 77 81 77 78 400 69 71 67 69 fluazinam 600 70 75 80 75 untreated control (disease index) (11) (10) (12) (11)

Efficacy calculation method is as follows:

${{Disease}\mspace{14mu} {index}\mspace{14mu} (\%)} = {\frac{\sum\begin{pmatrix} {{number}\mspace{14mu} {of}\mspace{14mu} {infected}\mspace{14mu} {leaves} \times} \\ {{corresponding}\mspace{14mu} {grading}} \end{pmatrix}}{{total}\mspace{14mu} {investigated}\mspace{14mu} {leaves} \times {highest}\mspace{14mu} {grading}} \times 100}$ ${{Efficacy}\mspace{14mu} (\%)} = {\frac{\begin{matrix} {{{control}\mspace{14mu} {disease}\mspace{14mu} {index}} -} \\ {{treatment}\mspace{14mu} {disease}\mspace{14mu} {index}} \end{matrix}}{{control}\mspace{14mu} {disease}\mspace{14mu} {index}} \times 100}$ 

1. Pyrazole amide compounds represented by the following formula (I):

Wherein: R₁ is selected from H, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂cyanoalkyl, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂haloalkylcarbonyl, C₁-C₁₂alkoxycarbonyl, C₁-C₁₂haloalkoxycarbonyl, C₁-C₁₂alkylaminocarbonyl, C₁-C₁₂haloalkylaminocarbonyl, C₃-C₆cycloalkyl or R_(a); R₂ is selected from H, halogen, CN, C₁-C₁₂cyanoalkyl, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂cyanoalkoxy, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂haloalkoxyC₁-C₁₂alkyl, C₁-C₁₂alkylthioC₁-C₁₂alkyl, C₁-C₁₂haloalkylthioC₁-C₁₂alkyl, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₃-C₆cycloalkyl or R₈; R₃ is selected from H or C₁-C₁₂alkyl; m is selected from 0 to 5; R₄ is selected from halogen, CN, CONH₂, CSNH₂, NO₂, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂haloalkoxyC₁-C₁₂alkyl, C₁-C₁₂alkylthioC₁-C₁₂alkyl, C₁-C₁₂haloalkylthioC₁-C₁₂alkyl, C₁-C₁₂alkylamino, C₁-C₁₂haloalkylamino, C₂-C₁₂dialkylamino, piperidyl, pyrrolidyl, N-methyl piperazinyl, morpholinyl, C₂-C₁₂alkenyl, C₂-C₁₂haloalkenyl, C₂-C₁₂alkenoxy, C₂-C₁₂haloalkenoxy, C₂-C₁₂alkynyl, C₂-C₁₂haloalkynyl, C₂-C₁₂alkynoxy, C₂-C₁₂haloalkynoxy, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl or R₈; n is selected from 0 to 4; R₅ is selected from H, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₃-C₆cycloalkyl, C₁-C₁₂cyanoalkyl, C₁-C₁₂alkylamino, C₁-C₁₂haloalkylamino, C₂-C₁₂dialkylamino, C₂-C₁₂alkenyl, C₂-C₁₂haloalkenyl, C₂-C₁₂alkynyl, C₂-C₁₂haloalkynyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂haloalkylcarbonyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkylcarbonylamino,

or R₈; R₆ is selected from H, CN, SCN, H(C═O), C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₁-C₁₂alkylcarbonyl, C₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂cyanoalkyl, C₁-C₁₂hydroxyalkyl, C₃-C₆cycloalkyl or R₈; p is selected from 0 to 5; X₁ is selected from H, halogen, NO₂, CN, SCN, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylsulfinyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₁₂haloalkylthio, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂haloalkoxyC₁-C₁₂alkyl, C₁-C₁₂alkylthioC₁-C₁₂alkyl or C₁-C₁₂haloalkylthioC₁-C₁₂alkyl; X₂, X₃, X₄ and X₅ may be the same or different, mutually independently selected from H, halogen, CN, NO₂, OH, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio or C₁-C₁₂alkylsulfonyl; Q₁ and Q₂ may be the same or different, mutually independently selected from H, NH₂, OH, CN, SCN, C₁-C₁₂cyanoalkyl, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylsulfinyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₁₂alkylamino, C₂-C₁₂dialkylamino, piperidyl, pyrrolidyl, N-methyl piperazinyl, morpholinyl, H(C═O), C₁-C₁₂alkylaminocarbonyl, C₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkylaminothio, C₂-C₁₂dialkylaminothio, C₃-C₆cycloalkyl or R₈; Y is selected from O, S or NR₇; Z is selected from O or S; R₇ is selected from H, CN, NH₂, OH, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₃-C₆cycloalkyl, C₁-C₁₂cyanoalkyl, C₁-C₁₂cyanoalkoxy, C₁-C₁₂alkylamino, C₁-C₁₂haloalkylamino, C₂-C₁₂dialkylamino, piperidyl, Pyrrolidyl, N-methylpiperazinyl, morpholinyl, 2,6-dimethylmorpholinyl, C₂-C₂alkenyl, C₂-C₁₂haloalkenyl, C₂-C₁₂alkenoxy, C₂-C₁₂haloalkenoxy, C₂-C₁₂alkynyl, C₂-C₁₂haloalkynyl, C₂-C₁₂alkynoxy, C₂-C₁₂haloalkynoxy, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂haloalkylcarbonyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkylcarbonylamino,

or R₈; Or, when Y is selected from NR₇, NR₇ and R₅ form a unsubstituted or substituted five-membered or six-membered ring with 1-4 substitutents selected independently from C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy or C₃-C₆cycloalkyl; R₈ is selected from phenyl, benzoyl, phenoxycarbonyl, phenylaminocarbonyl, phenylC₁-C₆alkyl, naphthyl, naphthylC₁-C₆alkyl, heteroaryl, heteroarylcarbonyl, heteroaryloxycarbonyl, heteroarylaminocarbonyl or heteroarylC₁-C₆alkyl, which can be unsubstituted or further substituted with 1-5 substitutents, the substitutent(s) mentioned was (were) selected independently from halogen, NO₂, CN, SH, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₃-C₁₂cycloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₂-C₁₂alkenyl, C₂-C₁₂haloalkenyl, C₂-C₁₂alkynyl, C₂-C₁₂haloalkynyl, C₃-C₁₂alkenoxy, C₃-C₁₂haloalkenoxy, C₃-C₁₂alkynoxy, C₃-C₁₂haloalkynoxy, C₁-C₁₂alkylsulfinyl, C₁-C₁₂haloalkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂haloalkylcarbonyl, C₁-C₁₂alkylcarbonyloxy, C₁-C₁₂alkylcarbonylamino, C₁-C₁₂alkylsulfonyloxy, C₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkoxyC₁-C₁₂alkoxy, C₁-C₁₂ alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkoxycarbonylamino, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkoxy, CHO, CO₂H, CO₂Na, CO₂NH₄, NR₉R₁₀, C(═O)NR₉R₁₀, OC(═O)NR₉R₁₀, C(═S)NR₉R₁₀ or SO₂NR₉R₁₀; R₉ and R₁₀ may be the same or different, mutually independently selected from H, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₃-C₆ cycloalkyl or R₈; (CHR₃)mCON(Q₂) links with phenyl ring at the 2, 3 or 4-position.
 2. The compounds according to the claim 1, characterized in that wherein general formula (I): R₁ is selected from H, C₁-C₆ alkyl, C₁-C₆haloalkyl, C₁-C₆cyanoalkyl, C₁-C₆alkoxyC₁-C₆alkyl, C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆haloalkoxycarbonyl, C₁-C₆alkylaminocarbonyl, C₁-C₁₀haloalkylaminocarbonyl, C₃-C₆cycloalkyl or R₈; R₂ is selected from H, halogen, CN, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆cyanoalkoxy, C₁-C₆alkylthio, C₁-C₆alkoxyC₁-C₆alkyl, C₁-C₆haloalkoxyC₁-C₆alkyl, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₃-C₆cycloalkyl or R₈; R₃ is selected from H or C₁-C₄alkyl; m is selected from 1 to 3; R₄ is selected from halogen, CN, CONH₂, CSNH₂, NO₂, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkoxyC₁-C₄alkyl, C₁-C₄haloalkoxyC₁-C₄alkyl, C₁-C₄alkylthioC₁-C₄alkyl, C₁-C₄haloalkylthioC₁-C₄alkyl, C₁-C₄alkylamino, C₁-C₄haloalkylamino, C₂-C₄dialkylamino, piperidyl, Pyrrolidyl, N-methyl piperazinyl, morpholinyl, C₂-C₄alkenyl, C₂-C₄haloalkenyl, C₂-C₄alkenoxy, C₂-C₄haloalkenoxy, C₂-C₄alkynyl, C₂-C₄haloalkynyl, C₂-C₄alkynoxy, C₂-C₄haloalkynoxy, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl or R₈; n is selected from 0 to 3; R₅ is selected from H, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxyC₁-C₄alkyl, C₃-C₆cycloalkyl, C₁-C₄cyanoalkyl, C₁-C₄alkylamino, C₁-C₄haloalkylamino, C₂-C₆dialkylamino, C₂-C₄alkenyl, C₂-C₄haloalkenyl, C₂-C₄alkynyl, C₂-C₄haloalkynyl, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfonyl, C₁-C₄alkylcarbonyl, C₁-C₄haloalkylcarbonyl, C₁-C₄alkyloxycarbonylC₁-C₄alkyl, C₁-C₄alkylcarbonylamino,

or R₈; R₆ is selected from H, CN, SCN, H(C═O), C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylcarbonyl, C₁-C₄alkyloxycarbonyl, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄cyanoalkyl, C₁-C₄hydroxyalkyl, C₃-C₆cycloalkyl or R₈; p is selected from 0 to 4; X₁ is selected from H, halogen, NO₂, CN, SCN, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄haloalkylthio, C₁-C₄alkoxyC₁-C₄alkyl, C₁-C₄haloalkoxyC₁-C₄alkyl, C₁-C₄alkylthioC₁-C₄alkyl or C₁-C₄haloalkylthioC₁-C₄alkyl; X₂, X₃, X₄ and X₅ may be the same or different, mutually independently selected from H, halogen, CN, NO₂, OH, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio or C₁-C₄alkylsulfonyl; Q₁ and Q₂ may be the same or different, mutually independently selected from H, NH₂, OH, CN, SCN, C₁-C₄cyanoalkyl, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkylcarbonyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkoxyC₁-C₄alkyl, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄alkylamino, C₂-C₆dialkylamino, piperidyl, Pyrrolidyl, N-methylpiperazinyl, morpholinyl, H(C═O), C₁-C₄alkylaminocarbonyl, C₁-C₄alkoxycarbonyl, C₁-C₄alkylaminothio, C₂-C₄dialkylaminothio, C₃-C₆cycloalkyl or R₈; Y is selected from O, S or NR₇; Z is O; R₇ is selected from H, CN, NH₂, OH, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₃-C₆cycloalkyl, C₁-C₄cyanoalkyl, C₁-C₄cyanoalkoxy, C₁-C₄alkylamino, C₁-C₄haloalkylamino, C₂-C₄dialkylamino, piperidyl, pyrrolidyl, N-methylpiperazinyl, morpholinyl, 2,6-dimethylmorpholinyl, C₂-C₄alkenyl, C₂-C₄haloalkenyl, C₂-C₄alkenoxy, C₂-C₄haloalkenoxy, C₂-C₄alkynyl, C₂-C₄haloalkynyl, C₂-C₄alkynoxy, C₂-C₄haloalkynoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfonyl, C₁-C₄alkylcarbonyl, C₁-C₄haloalkylcarbonyl, C₁-C₄alkoxycarbonylC₁-C₄alkyl, C₁-C₄alkylcarbonylamino,

or R₈; Or, when Y is selected from NR₇, NR₇ and R₅ form a unsubstituted or substituted five-membered or six-membered ring with 1-2 substitutents selected independently from C₁-C₃alkyl; R₈ is selected from phenyl, benzoyl, phenoxycarbonyl, phenylaminocarbonyl, benzyl, phenethyl, naphthyl, pyridyl, picolyl, pyridylethyl, pyrimidyl, pyridazinyl, pyrazinyl, cyanuro, unsym-triazinyl, furanyl, thienyl, pyrrolyl, thiazolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadizolyl, benzofuryl, benzothiophenyl, benzothiazolyl, benzoxazolyl, benzoxazolylmethyl, benzopyranyl, benzopyronyl, benzopyridazinyl, indolyl, quinolyl, quinoxalinyl, triazolopyrimidinyl, imidazopyridinyl, imidazothiazolyl, purinyl, pyridylformoxyl, pyrimidinylformoxyl, pyridyloxycarbonyl, pyrimidinyloxycarbonyl, pyridylaminocarbonyl, pyrimidinylaminocarbonyl or thiazolylmethyl, which can be unsubstituted or further substituted with 1-3 substitutents, the substitutent(s) mentioned was (were) selected independently from halogen, NO₂, CN, SH, C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₆cycloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₂-C₄alkenyl, C₂-C₄haloalkenyl, C₂-C₄alkynyl, C₂-C₄haloalkynyl, C₃-C₆alkenoxy, C₃-C₆haloalkenoxy, C₃-C₆alkynoxy, C₃-C₆haloalkynoxy, C₁-C₄alkylsulfinyl, C₁-C₄haloalkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfonyl, C₁-C₄alkylcarbonyl, C₁-C₄haloalkylcarbonyl, C₁-C₄alkylcarbonyloxy, C₁-C₄alkylcarbonylamino, C₁-C₄alkylsulfonyloxy, C₁-C₄alkoxycarbonyl, C₁-C₄alkoxyC₁-C₄alkoxy, C₁-C₄alkoxycarbonylC₁-C₄alkyl, C₁-C₄alkoxycarbonylamino, C₁-C₄alkoxycarbonylC₁-C₄alkoxy, CHO, CO₂H, CO₂Na, CO₂NH₄, NR₉R₁₀, C(═O)NR₉R₁₀, OC(═O)NR₉R₁₀, C(═S)NR₉R₁₀ or SO₂NR₉R₁₀; R₉ and R₁₀ may be the same or different, mutually independently selected from H, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₃-C₆cycloalkyl or R₈; (CHR₃)mCON(Q₂) links with phenyl ring at the 2, 3 or 4-position.
 3. The compounds according to the claim 2, characterized in that wherein general formula (I): R₁ is selected from H, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxyC₁-C₄alkyl, C₃-C₆cycloalkyl or R₈; R₂ is selected from H, chloride, bromine, fluorine, iodine, CN, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄cyanoalkoxy, C₁-C₄alkoxyC₁-C₄alkyl, C₁-C₄haloalkoxyC₁-C₄alkyl, C₃-C₆cycloalkyl or R₈; R₃ is selected from H, methyl or ethyl; m is selected from 1, 2 or 3; R₄ is selected from fluorine, chloride, bromine, iodine, CN, NO₂, C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylamino, C₂-C₄dialkylamino or C₁-C₃alkylsulfonyl; n is selected from 0, 1, 2 or 3; R₅ is selected from H, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxyC₁-C₃alkyl, C₃-C₆cycloalkyl, C₁-C₄cyanoalkyl, C₁-C₄alkylamino, C₂-C₆dialkylamino, C₃-C₄alkenyl, C₃-C₄alkynyl or R₈; R₆ is selected from H, CN, SCN, C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃alkylthio or C₁-C₃hydroxyalkyl; p is selected from 0, 1, 2 or 3; X₁ is selected from H, fluorine, chloride, bromine, iodine, NO₂, CN, SCN, C₁-C₃alkyl or C₁-C₃haloalkyl; X₂, X₃, X₄ and X₅ may be the same or different, mutually independently selected from H, fluorine, chloride, bromine, iodine, CN, NO₂, OH, C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy or C₁-C₃haloalkoxy; Q₁ and Q₂ may be the same or different, mutually independently selected from H, CN, SCN, C₁-C₃alkyl, C₁-C₃alkylcarbonyl, C₁-C₃alkoxyC₁-C₂alkyl or H(C═O); Y is selected from O or NR₇; Z is O; R₇ is selected from H, CN, NH₂, OH, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₃-C₆cycloalkyl, C₁-C₃cyanoalkyl, C₁-C₃cyanoalkoxy, C₁-C₃alkylamino, C₁-C₃haloalkylamino, C₂-C₄dialkylamino, piperidyl, pyrrolidyl, N-methylpiperazinyl, morpholinyl, 2,6-dimethylmorpholinyl, C₃-C₄alkenyl, C₃-C₄haloalkenyl, C₃-C₄alkenoxy, C₃-C₄haloalkenoxy, C₃-C₄alkynyl, C₃-C₄haloalkynyl, C₃-C₄alkynoxy, C₃-C₄haloalkynoxy, C₁-C₃alkylsulfonyl, C₁-C₃haloalkylsulfonyl or R₈; Or, when Y is selected from NR₇, NR₇ and R₅ form piperidine, tetrahydropyrrole, N-methylpiperazine, morpholine or 2,6-dimethylmorpholine; R₈ is selected from phenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 4-methylphenyl, 4-trifluoromethylphenyl, 4-methoxylphenyl, 2,6-dichloro-4-trifluoromethylphenyl, benzoyl, 4-chlorobenzoyl, 2,4-dichlorobenzoyl, 4-trifluoromethylbenzoyl, phenoxycarbonyl, 4-chlorophenoxycarbonyl, 2,4-dichlorophenoxycarbonyl, 4-trifluoromethylphenoxycarbonyl, phenylaminocarbonyl, 4-chlorophenylaminocarbonyl, 2,4-dichlorophenylaminocarbonyl, 4-trifluoromethyphenylaminocarbonyl, benzyl, 4-chlorobenzyl, 4-tert-butylbenzyl, 4-trifluoromethylbenzyl, phenethyl, 2-pyridyl, 3-chloro-2-pyridyl, 3,5-dichloro-2-pyridyl, 3,5,6-trichloro-2-pyridyl, 5-trifluoromethyl-2-pyridyl, 5-methyl-2-pyridyl, 3-chloro-5-cyano-2-pyridyl, 3-chloro-5-trifluoromethyl-2-pyridyl, 2-picolyl, 2-chloro-5-picolyl, 3-chloro-5-trifluoro-2-picolyl, 2-pyridinylethyl, 3-chloro-5-trifluoromethyl-2-pyridinylethyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, thiazole-2-yl, 2-chloro-5-thiazolylmethyl, 3-pyridylformoxyl, 2-chloro-3-pyridylformoxyl, 2-chloro-5-pyridylformoxyl, 2-pyrimidinylformoxyl, 5-trifluoromethyl-2-pyrimidinylformoxyl, 2-pyridyloxycarbonyl, 3-chloro-2-pyridyloxycarbonyl, 3,5-dichloro-2-pyridyloxycarbonyl, 5-trifluoromethyl-2-pyridyloxycarbonyl, 5-methyl-2-pyridyloxycarbonyl, 3-chloro-5-cyano-2-pyridyloxycarbonyl, 3-chloro-5-trifluoromethyl-2-pyridyloxycarbonyl, 2-pyrimidinyloxycarbonyl, 5-trifluoromethyl-2-pyrimidinyloxycarbonyl, 2-pyridylaminocarbonyl, 3-chloro-2-pyridylaminocarbonyl or 2-pyrimidinylaminocarbonyl; (CHR₃)mCON(Q₂) links with phenyl ring at the 2, 3 or 4-position.
 4. The compounds according to the claim 3, characterized in that wherein general formula (I): R₁ is selected from H, methyl, ethyl, n-propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, trifluoromethyl, trifluoroethyl, methoxymethyl, ethoxymethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or R₈; R₂ is selected from H, chloride, bromine, fluorine, CN, methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, trifluoromethyl, difluoromethyl, fluoromethyl, trifluoromethoxyl, trifluoroethoxyl, fluoromethoxyl, cyanomethoxyl, methoxymethyl, trifluoromethoxymethyl, trifluoroethoxymethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or R₈; R₃ is selected from H or methyl; m is 1; R₄ is selected from fluorine, chloride, bromine, iodine, CN, methyl, ethyl, trifluoromethyl, methoxyl, trifluoromethoxyl or methylsulfonyl; n is selected from 0, 1, 2 or 3; R₅ is selected from H, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, trifluoromethyl, trifluoroethyl, cyclopropyl, cyclohexyl, cyanomethyl, allyl, propargyl or R₈; R₆ is selected from H, CN, SCN, methyl or ethyl; p is selected from 0, 1, 2 or 3; X₁ is selected from H, fluorine, chloride, bromine, iodine, NO₂, methyl or chloromethyl; X₂, X₃, X₄ and X₅ may be the same or different, mutually independently selected from H, chloride, bromine or methoxyl; Q₁ and Q₂ are H; Y is selected from O or NR₇; Z is O; R₇ is selected from H, CN, NH₂, OH, methyl, ethyl, cyclopropyl, cyclopentyl, cyclohexyl, cyanomethyl, methylamino, dimethylamino, methylsulfonyl or R₈; Or, when Y is selected from NR₇, NR₇ and R₅ form piperidine, tetrahydropyrrole, N-methylpiperazine, morpholine or 2,6-dimethylmorpholine; R₈ is selected from phenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 4-methylphenyl, 4-trifluoromethylphenyl, 4-methoxylphenyl, 2,6-dichloro-4-trifluoromethylphenyl, benzyl, 4-chlorobenzyl, 4-tert-butylbenzyl, 4-trifluoromethylbenzyl, phenethyl, 2-pyridyl, 3-chloro-2-pyridyl, 3,5-dichloro-2-pyridyl, 3,5,6-trichloro-2-pyridyl, 5-trifluoromethyl-2-pyridyl, 5-methyl-2-pyridyl, 3-chloro-5-cyano-2-pyridyl, 3-chloro-5-trifluoromethyl-2-pyridyl, 2-picolyl, 2-chloro-5-picolyl, 3-chloro-5-trifluoromethyl-2-picolyl, 2-pyridinylethyl, 3-chloro-5-trifluoromethyl-2-pyridinylethyl, thiazole-2-yl, 2-chloro-5-thiazolylmethyl or 2-pyrimidinyl; (CHR₃)mCON(Q₂) links with phenyl ring at the 2, 3 or 4-position.
 5. The compounds according to the claim 4, characterized in that wherein general formula (I): R₂ is selected from bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, trifluoromethyl, cyclopropyl or 4-chlorophenyl; R₃ is selected from H or methyl; m is 1; R₄ is selected from fluorine, chloride, bromine, iodine, CN or methyl; n is selected from 0, 1 or 2; R₆ is selected from H or methyl; p is selected from 0, 1, 2 or 3; X₁ is selected from H, chloride or methyl; X₂, X₃, X₄, X₅, Q₁, Q₂ are H; Z is O; YR₅ is selected from amino, methylamino, ethylamino, dimethylamino, methoxyl, ethoxyl or morpholinyl; (CHR₃)mCON(Q₂) links with phenyl ring at the 2, 3 or 4-position.
 6. An intermediate or its salt used to prepare the compounds of the general formula (I) according to claim 1, their structures represented by the general formula (II):

Wherein: R₃ is selected from H or C₁-C₁₂alkyl; m is selected from 0 to 5; R₄ is selected from halogen, CN, CONH₂, CSNH₂, NO₂, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂haloalkoxyC₁-C₁₂alkyl, C₁-C₁₂alkylthioC₁-C₁₂alkyl, C₁-C₁₂haloalkylthioC₁-C₁₂alkyl, C₁-C₁₂alkylamino, C₁-C₁₂haloalkylamino, C₂-C₁₂dialkylamino, piperidyl, pyrrolidyl, N-methyl piperazinyl, morpholinyl, C₂-C₁₂alkenyl, C₂-C₁₂haloalkenyl, C₂-C₁₂alkenoxy, C₂-C₁₂haloalkenoxy, C₂-C₁₂alkynyl, C₂-C₁₂haloalkynyl, C₂-C₁₂alkynoxy, C₂-C₁₂haloalkynoxy, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl or R₈; n is selected from 0 to 4; R₅ is selected from H, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₃-C₆cycloalkyl, C₁-C₁₂cyanoalkyl, C₁-C₁₂alkylamino, C₁-C₁₂haloalkylamino, C₂-C₁₂dialkylamino, C₂-C₁₂alkenyl, C₂-C₁₂haloalkenyl, C₂-C₁₂alkynyl, C₂-C₁₂haloalkynyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂haloalkylcarbonyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkylcarbonylamino,

or R₈; R₆ is selected from H, CN, SCN, H(C═O), C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₁-C₁₂alkylcarbonyl, C₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂cyanoalkyl, C₁-C₁₂hydroxyalkyl, C₃-C₆cycloalkyl or R; p is selected from 0 to 5; X₂, X₃, X₄ and X₅ may be the same or different, mutually independently selected from H, halogen, CN, NO₂, OH, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio or C₁-C₁₂alkylsulfonyl; Q₁ and Q₂ may be the same or different, mutually independently selected from H, NH₂, OH, CN, SCN, C₁-C₁₂cyanoalkyl, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylsulfinyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₁₂alkylamino, C₂-C₁₂dialkylamino, piperidyl, pyrrolidyl, N-methyl piperazinyl, morpholinyl, H(C═O), C₁-C₁₂alkylaminocarbonyl, C₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, C₁-C₂alkylaminothio, C₂-C₁₂dialkylaminothio, C₃-C₆cycloalkyl or R₈; Y is selected from O, S or NR₇; Z is selected from O or S; R₇ is selected from H, CN, NH₂, OH, C₁-C₁₂alkyl, C₁-C₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₃-C₆cycloalkyl, C₁-C₂cyanoalkyl, C₁-C₂cyanoalkoxy, C₁-C₁₂alkylamino, C₁-C₁₂haloalkylamino, C₂-C₁₂dialkylamino, piperidyl, Pyrrolidyl, N-methylpiperazinyl, morpholinyl, 2,6-dimethylmorpholinyl, C₂-C₁₂alkenyl, C₂-C₁₂haloalkenyl, C₂-C₁₂alkenoxy, C₂-C₁₂haloalkenoxy, C₂-C₁₂alkynyl, C₂-C₁₂haloalkynyl, C₂-C₁₂alkynoxy, C₂-C₁₂haloalkynoxy, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂haloalkylcarbonyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkylcarbonylamino,

or R₈; Or, when Y is selected from NR₇, NR₇ and R₅ form a unsubstituted or substituted five-membered or six-membered ring with 1-4 substitutents selected independently from C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy or C₃-C₆cycloalkyl; R₈ is selected from phenyl, benzoyl, phenoxycarbonyl, phenylaminocarbonyl, phenylC₁-C₆alkyl, naphthyl, naphthylC₁-C₆alkyl, heteroaryl, heteroarylcarbonyl, heteroaryloxycarbonyl, heteroarylaminocarbonyl or heteroarylC₁-C₆alkyl, which can be unsubstituted or further substituted with 1-5 substitutents, the substitutent(s) mentioned was (were) selected independently from halogen, NO₂, CN, SH, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₃-C₁₂cycloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₂-C₁₂alkenyl, C₂-C₁₂haloalkenyl, C₂-C₁₂alkynyl, C₂-C₁₂haloalkynyl, C₃-C₁₂alkenoxy, C₃-C₁₂haloalkenoxy, C₃-C₁₂alkynoxy, C₃-C₁₂haloalkynoxy, C₁-C₁₂alkylsulfinyl, C₁-C₁₂haloalkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂haloalkylcarbonyl, C₁-C₁₂alkylcarbonyloxy, C₁-C₁₂alkylcarbonylamino, C₁-C₁₂alkylsulfonyloxy, C₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkoxyC₁-C₁₂alkoxy, C₁-C₁₂ alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkoxycarbonylamino, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkoxy, CHO, CO₂H, CO₂Na, CO₂NH₄, NR₉R₁₀, C(═O)NR₉R₁₀, OC(═O)NR₉R₁₀, C(═S)NR₉R₁₀ or SO₂NR₉R₁₀; R₉ and R₁₀ may be the same or different, mutually independently selected from H, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₃-C₆ cycloalkyl or R₈; (CHR₃)mCON(Q₂) links with phenyl ring at the 2, 3 or 4-position.
 7. A method of preparation of the compounds of general formula (I) (when Q₁=H) according to claim 1, the reaction routes are as follows:

Wherein: R₁ is selected from H, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂cyanoalkyl, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂haloalkylcarbonyl, C₁-C₁₂alkoxycarbonyl, C₁-C₁₂haloalkoxycarbonyl, C₁-C₁₂alkylaminocarbonyl, C₁-C₁₂haloalkylaminocarbonyl, C₃-C₆cycloalkyl or R₈; R₂ is selected from H, halogen, CN, C₁-C₁₂cyanoalkyl, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂cyanoalkoxy, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂haloalkoxyC₁-C₁₂alkyl, C₁-C₁₂alkylthioC₁-C₁₂alkyl, C₁-C₁₂haloalkylthioC₁-C₁₂alkyl, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₃-C₆cycloalkyl or R₈; R₃ is selected from H or C₁-C₁₂alkyl; m is selected from 0 to 5; R₄ is selected from halogen, CN, CONH₂, CSNH₂, NO₂, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂haloalkoxyC₁-C₁₂alkyl, C₁-C₁₂alkylthioC₁-C₁₂alkyl, C₁-C₁₂haloalkylthioC₁-C₁₂alkyl, C₁-C₁₂alkylamino, C₁-C₁₂haloalkylamino, C₂-C₁₂dialkylamino, piperidyl, pyrrolidyl, N-methyl piperazinyl, morpholinyl, C₂-C₁₂alkenyl, C₂-C₁₂haloalkenyl, C₂-C₁₂alkenoxy, C₂-C₁₂haloalkenoxy, C₂-C₁₂alkynyl, C₂-C₁₂haloalkynyl, C₂-C₁₂alkynoxy, C₂-C₁₂haloalkynoxy, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl or R₈; n is selected from 0 to 4; R₅ is selected from H, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₃-C₆cycloalkyl, C₁-C₁₂cyanoalkyl, C₁-C₁₂alkylamino, C₁-C₁₂haloalkylamino, C₂-C₁₂dialkylamino, C₂-C₁₂alkenyl, C₂-C₁₂haloalkenyl, C₂-C₁₂alkynyl, C₂-C₁₂haloalkynyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂haloalkylcarbonyl, C₁-C₁₂alkoxycarbonylC₁-C₂alkyl, C₁-C₁₂alkylcarbonylamino,

or R₈; R₆ is selected from H, CN, SCN, H(C═O), C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₁-C₁₂alkylcarbonyl, C₁-C₁₂alkoxycarbonyl, C₁-C₂alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂cyanoalkyl, C₁-C₁₂hydroxyalkyl, C₃-C₆cycloalkyl or R₈; p is selected from 0 to 5; X₁ is selected from H, halogen, NO₂, CN, SCN, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylsulfinyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₁₂haloalkylthio, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂haloalkoxyC₁-C₁₂alkyl, C₁-C₁₂alkylthioC₁-C₁₂alkyl or C₁-C₂haloalkylthioC₁-C₁₂alkyl; X₂, X₃, X₄ and X₅ may be the same or different, mutually independently selected from H, halogen, CN, NO₂, OH, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio or C₁-C₁₂alkylsulfonyl; Q₂ is selected from H, NH₂, OH, CN, SCN, C₁-C₁₂cyanoalkyl, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylsulfinyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₁₂alkylamino, C₂-C₁₂dialkylamino, piperidyl, pyrrolidyl, N-methyl piperazinyl, morpholinyl, H(C═O), C₁-C₁₂alkylaminocarbonyl, C₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkylaminothio, C₂-C₁₂dialkylaminothio, C₃-C₆cycloalkyl or R₈; Y is selected from O, S or NR₇; Z is selected from O or S; R₇ is selected from H, CN, NH₂, OH, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₃-C₆cycloalkyl, C₁-C₁₂cyanoalkyl, C₁-C₁₂cyanoalkoxy, C₁-C₁₂alkylamino, C₁-C₁₂haloalkylamino, C₂-C₁₂dialkylamino, piperidyl, Pyrrolidyl, N-methylpiperazinyl, morpholinyl, 2,6-dimethylmorpholinyl, C₂-C₁₂alkenyl, C₂-C₁₂haloalkenyl, C₂-C₁₂alkenoxy, C₂-C₁₂haloalkenoxy, C₂-C₁₂alkynyl, C₂-C₁₂haloalkynyl, C₂-C₁₂alkynoxy, C₂-C₁₂haloalkynoxy, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₁₂alkylcarbonyl, C₁-C₂haloalkylcarbonyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkylcarbonylamino,

or R₈; Or, when Y is selected from NR₇, NR₇ and R₅ form a unsubstituted or substituted five-membered or six-membered ring with 1-4 substitutents selected independently from C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy or C₃-C₆cycloalkyl; R₈ is selected from phenyl, benzoyl, phenoxycarbonyl, phenylaminocarbonyl, phenylC₁-C₆alkyl, naphthyl, naphthylC₁-C₆alkyl, heteroaryl, heteroarylcarbonyl, heteroaryloxycarbonyl, heteroarylaminocarbonyl or heteroarylC₁-C₆alkyl, which can be unsubstituted or further substituted with 1-5 substitutents, the substitutent(s) mentioned was (were) selected independently from halogen, NO₂, CN, SH, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₃-C₁₂cycloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₂-C₁₂alkenyl, C₂-C₁₂haloalkenyl, C₂-C₁₂alkynyl, C₂-C₁₂haloalkynyl, C₃-C₁₂alkenoxy, C₃-C₁₂haloalkenoxy, C₃-C₁₂alkynoxy, C₃-C₁₂haloalkynoxy, C₁-C₁₂alkylsulfinyl, C₁-C₁₂haloalkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂haloalkylcarbonyl, C₁-C₁₂alkylcarbonyloxy, C₁-C₁₂alkylcarbonylamino, C₁-C₁₂alkylsulfonyloxy, C₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkoxyC₁-C₁₂alkoxy, C₁-C₁₂ alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkoxycarbonylamino, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkoxy, CHO, CO₂H, CO₂Na, CO₂NH₄, NR₉R₁₀, C(═O)NR₉R₁₀, OC(═O)NR₉R₁₀, C(═S)NR₉R₁₀ or SO₂NR₉R₁₀; R₉ and R₁₀ may be the same or different, mutually independently selected from H, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₃-C₆ cycloalkyl or R₈; (CHR₃)mCON(Q₂) links with phenyl ring at the 2, 3 or 4-position.
 8. A method of controlling fungi which comprises applying the compound having general formula (I) according to claim 1 to agricultural and other fields.
 9. A fungicidal composition comprising the compound having general formula (I) of claim 1 as an active ingredient, wherein the weight percentage of the active ingredient in the composition is from 0.1-99%.
 10. A method of controlling fungi which comprises applying the composition according to claim 9 to agricultural and other fields.
 11. A method of controlling fungi which comprises applying the compound having general formula (I) according to claim 2 to agricultural and other fields.
 12. A fungicidal composition comprising the compound having general formula (I) of claim 2 as an active ingredient, wherein the weight percentage of the active ingredient in the composition is from 0.1-99%.
 13. A method of controlling fungi which comprises applying the composition according to claim 12 to agricultural and other fields.
 14. A method of controlling fungi which comprises applying the compound having general formula (I) according to claim 3 to agricultural and other fields.
 15. A fungicidal composition comprising the compound having general formula (I) of claim 3 as an active ingredient, wherein the weight percentage of the active ingredient in the composition is from 0.1-99%.
 16. A method of controlling fungi which comprises applying the composition according to claim 15 to agricultural and other fields.
 17. A method of controlling fungi which comprises applying the compound having general formula (I) according to claim 4 to agricultural and other fields.
 18. A fungicidal composition comprising the compound having general formula (I) of claim 4 as an active ingredient, wherein the weight percentage of the active ingredient in the composition is from 0.1-99%.
 19. A method of controlling fungi which comprises applying the composition according to claim 18 to agricultural and other fields.
 20. A method of controlling fungi which comprises applying the compound having general formula (I) according to claim 5 to agricultural and other fields.
 21. A fungicidal composition comprising the compound having general formula (I) of claim 5 as an active ingredient, wherein the weight percentage of the active ingredient in the composition is from 0.1-99%.
 22. A method of controlling fungi which comprises applying the composition according to claim 21 to agricultural and other fields. 